含氧萜烯的生产方法与流程

优先权本申请要求2015年8月21日提交的美国临时申请号62/040,284的权益和优先权，其据此通过引用整体并入本文。发明领域本发明涉及含氧的倍半萜烯(例如诺卡酮)及其生产和使用方法。本发明还提供了用于含氧的倍半萜烯(例如诺卡酮)的生产的酶，以及用于识别、选择、制备和使用这些酶的方法。发明背景食品和饮料行业以及其他行业诸如香水、化妆品和保健行业通常使用萜烯和/或类萜产品作为风味物和芳香物。作为示例，许多倍半萜烯化合物被用在香料(例如广藿香醇)和风味行业(例如诺卡酮)，并且许多是从植物中提取。然而，诸如以下因素：(i)植物原材料的可获得性和高价格；(ii)植物中相对低的萜烯含量；和(iii)为了在工业规模上生产足够量的萜烯产品的繁琐和低效的提取过程都激发了使用不依赖植物的系统的萜烯的生物合成的研究。因此，已经在开发用于将可再生资源诸如葡萄糖转化为类萜产品的技术到工程微生物上做出了努力。对比于传统方法，微生物具有无需土地以持续发展的快速生长的优势。许多微生物使用甲基赤藓糖醇4-磷酸(mep)途径或甲羟戊酸(mva)途径以提供生产类萜产品所必要的中间体。这些mep或mva途径可以包括内源性或工程化的mep或mva途径，或两者都包括。类异戊二烯途径工程和优化的详细理解公开在wo2011/060057、us2011/0189717、us2012/107893、us8,512,988和ajikumar等(2010)science33070-74中，这些文献中公开了包括诸如诺卡酮的倍半萜烯化合物的各种类萜化合物的生产，诺卡酮是产自朱栾倍半萜倍半萜烯底物的氧化的倍半萜烯。诺卡酮(4,4a,5,6,7,8-六氢-6-异丙烯基-4,4a-二甲基-2(3ii)-萘酮)是葡萄柚的重要风味成分，并且在商业上用于给软饮品和其他饮料提供风味，也被用于香料中。用于诺卡酮制备的常规方法是通过朱栾倍半萜的氧化(参见us6,200,786和us8,097,442)。原料朱栾倍半萜是昂贵的，并且因此消耗朱栾倍半萜的方法在商业上接受度不高。由于这些缺点，需要具有商业可行性和可持续的方法以制备诺卡酮和相关产品。发明概述本发明的一个目的是提供含氧的倍半萜烯产物的可持续生产。特别地，本发明提供了用于某些含氧的倍半萜烯的离体或体内生产的酶催化剂。在一些实施方案中，本发明提供了经工程化以用于含氧的倍半萜烯的生物合成的宿主细胞。本发明的另一个目的是提供用于合成含氧的倍半萜烯(包括在一些实施方案中功能表达)的工程化的细胞色素p450(cyp450)酶，以及大肠杆菌(e.coli)、酵母或其他宿主细胞中的还原酶对应物。本发明从而利用这种酶的独特性能进行氧化化学。一方面，本发明提供了制备倍半萜烯的含氧产物的方法。所述方法包括使倍半萜烯与具有倍半萜烯氧化活性的甜菊(steviarebaudiana)贝壳杉烯氧化酶(srko)或其衍生物接触。令人惊奇的是，野生型srko酶显示对于倍半萜烯底物的活性，但是它的天然活性被理解为作用于二萜烯底物。进一步地，srko酶对于酮、诺卡酮)显示出包括氧化的独特活性，这需要两个氧合循环，并且生产不同的含氧的萜烯产品，包括羟基大根香叶-1(10)5-二烯(hydroxygermacra-1(10)5-diene)和依兰烷-3,9(11)二烯-10-过氧化物(murolan-3,9(11)diene-10-peroxy)。这些活性区别于其他测试的p450酶，其他测试的p450酶仅产生羟基化产物(例如β-诺特卡醇)的一种立体异构体作为主要产品和/或仅产生少量的诺卡酮。在一些实施方案中，所述方法在离体(例如，无细胞)系统中发生。在其他实施方案中，倍半萜烯底物和srko或其衍生物在表达srko的细胞中接触，诸如细菌(例如大肠杆菌)。可以回收倍半萜烯的含氧产物，或倍半萜烯的含氧产物可以是用于进一步化学转化的底物。野生型的细胞色素p450在大肠杆菌中的功能表达具有归因于细菌平台的固有限制(诸如缺乏电子转移机制和细胞色素p450还原酶，以及由于缺乏内质网，p450酶的膜信号模块的翻译不相容性)。因此，在一些实施方案中，srko酶被修饰而在大肠杆菌宿主细胞中进行功能表达，例如，通过用稳定与大肠杆菌内膜的相互作用和/或降低细胞应激的短肽序列替换srko的n端跨膜区的一部分。在一些实施方案中，srko衍生物相对于野生型srko具有增加朱栾倍半萜氧化酶活性(例如，增加诺卡酮的产量)的至少一个突变。例如，srko相对于野生型srko(seqidno:37)或针对大肠杆菌中的表达和活性被修饰的srko(例如，seqidno:38_或55)可以具有1-50个独立选自替换、缺失或插入的突变。例如，srko衍生物相对于srko(seqidno:37、38或55)可以具有1-40个突变、1-30个突变、1-20个突变或1-10个突变。在这些或其他实施方案中，srko衍生物可以包含与srko(seqidno:37、38或55)具有至少50％序列同一性、或至少60％序列同一性、或至少70％序列同一性、或至少80％序列同一性、或至少90％序列同一性的氨基酸序列，并且具有朱栾倍半萜氧化酶活性。在各种实施方案中，srko在离体或细菌系统(例如，大肠杆菌)中保持朱栾倍半萜氧化酶活性，或对比于野生型酶具有增加的朱栾倍半萜氧化酶活性。可以维持或提高朱栾倍半萜氧化酶活性的srko的各种突变列于表2和表6。因此，在各种实施方案中，srko可以具有选自表2和/或表6的至少2个、至少3个、至少4个、至少5个、至少6个、至少7个、至少8个、至少9个或至少10个突变。srko的示例衍生物，在本文中也被称为“朱栾倍半萜氧化酶”或“vo”，由seqidno:104和105表示，它们可以进一步被衍生化以改善所需活性。可以根据经验选择突变，或通过计算机评估(insilicoevaluation)选择突变，或通过两者选择突变，以增加含氧的倍半萜烯滴度。根据本发明的方面，含氧的倍半萜烯产物可通过将倍半萜烯底物与具有朱栾倍半萜氧化活性的甜菊贝壳杉烯氧化酶(srko)或其衍生物接触而获得。不像其他的cyp450酶，当srko酶与朱栾倍半萜倍半萜烯底物一起使用时，产生可包括羟基大根香叶-1(10)5-二烯、依兰烷-3,9(11)二烯-10-过氧化物、诺特卡醇和诺卡酮的不同的含氧的萜烯产物谱。通过对比，其他的具有使朱栾倍半萜羟基化的活性的cyp450不生产大量的酮(诺卡酮)，这需要两个氧化循环。参见表4和图7。在各种实施方案中，倍半萜烯底物是(或主要的倍半萜烯底物是)朱栾倍半萜、大根香叶烯(a、b、c、d或e)、法尼烯、法尼醇、诺特卡醇、广藿香醇、杜松烯、雪松醇、蛇麻烯、长叶烯、和/或佛手柑油烯、β-衣兰烯、β-檀香醇、β-檀香烯、α-檀香烯、α-檀香醇、β-香根酮、a-香根酮、客烯醇、红没药烯、β-丁香烯(β-aryophyllene)、长叶烯；α-甜橙醛；α-红没药醇、(-)-β-可巴烯、(-)-α-可巴烯、4(z),7(z)-癸二烯醛(4(z),7(z)-ecadienal)、雪松醇、雪松烯、雪松醇、愈创木醇、(-)-6,9-愈创木二烯、布藜醇、愈创木醇、喇叭烯、喇叭茶醇、香樟烯和α-佛手柑油烯。在一些实施方案中，主要的倍半萜烯底物是朱栾倍半萜，并且主要的含氧产物是诺卡酮和/或诺特卡醇。本发明，当体内应用时，适用于广泛的宿主细胞。在一些实施方案中，宿主细胞是微生物宿主，诸如选自大肠杆菌、枯草芽孢杆菌(bacillussubtillus)或恶臭假单胞菌(pseudomonasputida)的细菌；或酵母，诸如酵母属(saccharomyces)、毕赤酵母属(pichia)或耶氏酵母属(yarrowia)的种类，包括酿酒酵母(saccharomycescerevisiae)、巴斯德毕赤酵母(pichiapastoris)和解脂耶氏酵母(yarrowialipolytica)。在一些实施方案中，宿主细胞产生异戊烯焦磷酸(ipp)，ipp用作合成倍半萜烯的底物。在一些实施方案中，ipp经内源性或外源性甲基赤藓糖醇磷酸(mep)或甲羟戊酸(mva)途径由代谢通量生产。在一些实施方案中，倍半萜烯至少部分经mep途径由代谢通量生产，并且其中宿主细胞具有至少一个额外拷贝的dxs、ispd、ispf和/或idi基因。在一些实施方案中，宿主细胞表达法尼基焦磷酸合成酶(fpps)，其由ipp或dmapp生产法尼基焦磷酸(fpp)。宿主细胞可以进一步表达异源倍半萜烯合成酶以生产所需的倍半萜烯支架。例如，在一些实施方案中，细胞表达朱栾倍半萜合成酶。已知几种朱栾倍半萜合成酶，包括葡萄(vitisvinifera)朱栾倍半萜合成酶(vvvs)(seqidno:1)或甜橙(citrussinensus)朱栾倍半萜合成酶(csvs)(seqidno:12)，本发明可以采用vvvs或csvs，或vvvs或csvs的衍生物。本文公开了示例性的衍生物vvvs酶。在某些实施方案中，如本文所公开，倍半萜烯合成酶是选自vv1m1(seqidno:3)、vv2m1(seqidno:5)、vv1m5(seqidno:7)、vv2m5(seqidno:9)或vs2(seqidno:11)的朱栾倍半萜合成酶。srko或其衍生物作用于倍半萜烯(例如，朱栾倍半萜)以生产含氧的萜烯产品。在一些实施方案中，srko是与细胞色素p450还原酶配偶体的融合蛋白(例如，srcpr)，允许辅因子有效再生。在其他的实施方案中，在宿主细胞中p450还原酶单独地提供(例如，到体外系统)或表达，并且在一些实施方案中，p450还原酶可以在与srko相同的操纵子中表达。在一些实施方案中，cpr酶单独地表达，并且在一些实施方案中，基因可以整合到宿主细胞基因组中。本文中公开了各种示例性cpr酶，并且该cpr酶可以被衍生化以改善含氧的类倍半萜烯滴度和/或改善p450效率。在一些实施方案中，宿主细胞表达一种或多种进一步将含氧的产物导向为诺卡酮的酶，诸如一种或多种醇脱氢酶(adh)的表达。本文公开了示例性的adh酶。在其他方面，本发明提供了用于制备含有含氧的倍半萜烯的产品的方法，所述方法包括将根据本文描述的方法制备并回收的含氧的倍半萜烯掺入消费品或工业产品。例如，产品可以是风味产品、芳香产品、化妆品、清洁产品、洗涤剂或肥皂或害虫防治产品。在一些实施方案中，回收的含氧产物包含诺卡酮，并且所述产品是选自饮料、口香糖、糖果或风味添加剂的风味产品。在其他方面，本发明提供了与野生型对比具有提高的朱栾倍半萜氧化酶活性的工程化srko酶，以及生产本文所述的含氧的倍半萜烯并且表达所有用于从异戊烯焦磷酸(ipp)生产所需的含氧的倍半萜烯的酶组分的宿主细胞。例如，在各种实施方案中，宿主细胞表达法尼基焦磷酸合成酶、倍半萜烯合成酶和srko或其衍生物。ipp可以通过mep和/或mva途径生产，ipp对于宿主细胞来说可以是内源的，并且可以通过途径中的异源酶的表达或某些酶的复制来提高。宿主细胞包括如本文所述的各种细菌和酵母。含氧的倍半萜烯(例如，诺卡酮和/或诺特卡醇)可以从培养物中回收，和/或任选地可以用作在细胞中或离体系统中进一步化学转化的底物。在另一方面，本发明提供了由本文所述的方法和宿主细胞生产的含倍半萜烯的油。在一些实施方案中，所述油包含羟基大根香叶-1(10)5-二烯、依兰烷-3,9(11)二烯-10-过氧化物、诺特卡醇和诺卡酮。在一些实施方案中，主要的朱栾倍半萜的含氧产物是诺卡酮和/或诺特卡醇。在另一方面，提供了基于p45017a1(其催化雄激素的生物合成)的结构坐标的srko晶体模型结构(cms)。图8a和8b中说明cms，包括包含萜烯结合口袋(tbp)的萜烯结合口袋结构域(tbd)和结合到tbd的萜烯(例如，朱栾倍半萜)。这种srko晶体模型结构(cms)促进srko衍生物的计算机测试(in-silicotesting)。在由这个同源模型的部分辅助中，本公开说明了使用几种突变策略来识别倍半萜烯氧化活性的增加或改善，突变策略包括回归共识诱变(back-to-consensusmutagenesis)、位点饱和诱变和重组文库筛选。本发明的其它方面和实施方案将从以下详细描述中显而易见。附图简述图1显示了用于朱栾倍半萜的生物合成的流程，朱栾倍半萜是根据本公开的srko的底物。图2描述了用于对vvvs进行的定点突变体的倍数生产力。225个点突变中的46个与野生型wtvvvs相比，传达了朱栾倍半萜的生产力平均提高至少20％。图2显示了相对于野生型，显示出一定水平的生产力(x轴)的vvvs突变体的数量(y轴)。图3(a和b)提供了朱栾倍半萜合成酶的氨基酸和核苷酸序列。图3a显示了葡萄野生型(wt)(vvvs)(seqidno:1和2)和衍生物vv1m1(seqidno:3和4)、vv2m1(seqidno:5和6)、vv1m5(seqidno:7和8)、vv2m5(seqidno:9和10)的氨基酸和核苷酸序列，以及衍生物vs2的氨基酸序列(seqidno:11)；以及甜橙野生型(csvs)的氨基酸序列(seqidno:12)。图3b显示了野生型vvvs和csvs序列以及工程化的vv2m5和vs2序列的比对。图4(a和b)提供了对于倍半萜烯支架具有活性的各种cyp450(细胞色素p450)酶的氨基酸和核苷酸序列。图4a显示了野生型氨基酸序列以及工程化用于细菌表达的氨基酸和核苷酸序列的序列：zzho(分别地，seqidno:13、14和15)、bsgao(分别地，seqidno:16、17和18)、hmpo(分别地，seqidno:19、20和21)、lsgao(分别地，seqidno:22、23和24)、nteao(分别地，seqidno:25、26和27)、cpvo(分别地，seqidno:28、29和30)、aaao(分别地，seqidno:31、32和33)、atko(分别地，seqidno:34、35和36)、srko(分别地，seqidno:37、38和39)、ppko(分别地，seqidno:40、41和42)、bmvo(分别地，seqidno:43和seqidno:44)、psvo(分别地，seqidno:45和seqidno:46)、polo(分别地，seqidno:47和seqidno:48)、civo(分别地，seqidno:49、50和51)、hagao(分别地，seqidno:52、53和54)。图4b显示了基于srko支架的工程化的朱栾倍半萜氧化酶的氨基酸序列(seqidno:55-61)。图5a和5b描述了大肠杆菌中表达mep、萜烯和类萜合成酶以及p450酶的构建体设计。图5a显示了上游mep途径基因的菌株构型和具有下游途径基因的两种质粒。图5b显示了p450融合体的构建，由此p450和cpr(细胞色素p450还原酶)的n端区域被截短，并且添加到示例性前导序列(malllavf--seqidno:112)(8rp)，同时两者与短连接子肽融合。图6(a-d)提供了利用序列比对的各种cpr(细胞色素p450还原酶)的氨基酸和核苷酸序列。在图6a中：甜菊(sr)cpr(seqidno:62和63)、甜菊(sr)cpr1(seqidno:76和77)、拟南芥(arabidopsisthaliana)(at)cpr(seqidno:64和65)、红豆杉(taxuscuspidata)(tc)cpr(seqidno:66和67)、青蒿(artemisiaannua)(aa)cpr(seqidno:68和69)、拟南芥(at)cpr1(seqidno:70和71)、拟南芥(at)cpr2(seqidno:72和73)、拟南芥(at)r2(seqidno:74和75)；甜菊(sr)cpr2(seqidno:78和79)；甜菊(sr)cpr3(seqidno:80和81)；香叶天竺葵(pelargoniumgraveolens)(pg)cpr(seqidno:82和83)。图6b显示了拟南芥和青蒿cpr序列的氨基酸序列(seqidno:72、74、68、64和70)的比对。图6c显示了甜菊cpr序列(seqidno:78、80、62和76)的比对。图6d显示了8个cpr氨基酸序列(seqidno:74、72、82、68、80、62、78和76)的比对。图7提供了gc色谱图，其显示了各种cyp450酶的不同活性，如实施例2中所述，与cpr配偶体表达在生产朱栾倍半萜的大肠杆菌中。将菌株培养4天，并用甲基叔丁基醚(mtbe)提取。通过gc-ms注射1μl的mtbe，并通过与ms文库比较来监测产物谱。从顶部到底部：紫杉属5-α羟化酶、菊苣(cichoriumintybus)(civo)p450(seqidno:50)、莨菪(hyoscyamusmuticus)(hmpo)p450(seqidno:20)和srko(seqidno:38)。图8a和8b说明了srko的同源性模型及其活性位点。srko同源模型基于已知的突变体p45017a1(如在devorenm和scottee(nature,482,116-119,2012)中公开的膜结合细胞色素p45017a1的晶体结构，其催化了人中雄激素的生物合成。血红素的位置以条棒显示。图8b描述了srko活性位点的结构模型，朱栾倍半萜以其α结合模式停靠。显示了二级结构基序(b-c环和i-螺旋)和靶向诱变的氨基酸。图9显示了优化朱栾倍半萜氧化酶(vo)n端膜锚定。选择大肠杆菌yhcb的n端作为膜锚定序列，其提供单次跨膜螺旋。筛选锚定的长度(20-24个氨基酸)和von端截短长度(28-32个氨基酸)以改善氧合滴度。图10显示了29的截短长度和基于大肠杆菌yhcb的20个氨基酸的n端锚定导致总氧合滴度相比于对照的平均值增加1.2倍。图11说明了在宿主细胞中表达的示例性下游途径，该途径用于将法尼基二磷酸转化为诺卡酮。法尼基二磷酸(通过表达的法尼基焦磷酸合成酶由ipp/dmapp产生)通过朱栾倍半萜合成酶(vs)的作用转化为朱栾倍半萜，朱栾倍半萜通过朱栾倍半萜氧化酶(vo)诸如srko或本文所述的工程化衍生物来氧化。vo辅因子通过细胞色素p450还原酶(cpr)再生。通过vo氧化的产物可以包括诺特卡醇和诺卡酮，可通过醇脱氢酶(adh)的作用进一步被导向为诺卡酮。图12显示了表达vo1-l-srcpr的菌株的氧合谱。氧合谱包括β-诺特卡醇和α-诺特卡醇的单一氧合产物以及两步氧合产物诺卡酮。图13(a和b)显示了在野生型srko中使用回归共识策略识别的突变，翻译成工程化的朱栾倍半萜氧化酶背景(n22yhcb_t30vo1)的评估。超过50％的突变导致总氧合滴度提高1.2-1.45倍。图(a)显示了以mg/l计的滴度。图(b)显示了氧合滴度的倍数变化。图14显示了回归共识突变、n端锚定优化和位点饱和诱变(ssm)的二级筛选的结果。识别出显示氧合滴度改善1.1-1.4倍的几个突变。图15显示了在33℃下选择vo1变体的性能。识别出在33℃下保持改善的生产力的六个突变。图16(a和b)显示了来自重组文库的初步筛选的结果。几个变体(所示的)在氧合产物滴度上表现出高达1.35倍的改善。在谱中有转变为更多的(+)-诺卡酮和更高的氧合能力用于选择变体。图(a)显示了以mg/l计的氧合产物。图(b)绘制了氧合能力的倍数变化(诺特卡醇仅需要来自朱栾倍半萜的一个氧合循环，而诺卡酮需要两个氧合循环)。图17显示了在34℃和37℃下对于选择的vo重组文库变体的氧合能力。图18显示了在重新筛选前导vo变体后在34℃和37℃下的氧合滴度。c6(1)(r76k、m94v、t131q、i390l、t468i)在37℃下具有最高的氧合能力，并被命名为vo2。图19显示了用于提高朱栾倍半萜氧化酶活性(30℃)的细胞色素p450还原酶(cpr)直系同源物的筛选。srcpr3显示了增加的氧合滴度和更高的诺卡酮产量。图20显示了在34℃下的cpr直系同源物的筛选。srcpr3和aacpr表现出约1.3倍的氧合滴度的改善，即使在更高的温度下。图21显示了在醇脱氢酶的作用下诺特卡醇向诺卡酮的转化。识别了四种adh直系同源物(vvdh、csaba2、bddh和zzsdr)，它们将诺特卡醇转化为(+)-诺卡酮，导致(+)-诺卡酮滴度增加3倍。图22(a和b)描述了醇脱氢酶。图22a显示了氨基酸和核苷酸序列，包括红串红球菌(rhodococcuserythropolis)(re)cdh(seqidno:84和85)、甜橙(cs)dh(seqidno:86和87)、甜橙(cs)dh1(seqidno:88和89)、甜橙(cs)dh2(seqidno:90和91)、甜橙(cs)dh3(seqidno:92和93)、葡萄(vv)dh(seqidno:94和95)、葡萄(vv)dh1(seqidno:96和97、甜橙(cs)aba2(seqidno:98和99)、短柄草(brachypodiumdistachyon)(bd)dh(seqidno:100和101)、红球姜(zingiberzerumbet)(zz)sdr(seqidno:102和103)的那些氨基酸和核苷酸序列。图22b显示了氨基酸序列的比对。图23(a和b)显示了几种工程化的朱栾倍半萜氧化酶(vo)变体的比对。在图23a中：8rp-t20srko(seqidno:106)是在n端具有20个氨基酸截短，并且添加了8个氨基酸的膜锚定的srko序列。8rp-t20vo0(seqidno:107)具有srko的n端的20个氨基酸的截短、8个氨基酸的n端锚定的添加和499位的单突变(根据野生型srko编号)。n22yhcb-t30vo1(seqidno:104)具有srko的n端的30个氨基酸的截短、基于来自大肠杆菌yhcb的22个氨基酸的膜锚定、以及在位置46、231、284、383、400、444、488和499的8个点突变(相对于srko野生型)。n22yhcb-t30vo2(seqidno:105)具有srko的n端的30个氨基酸的截短、基于来自大肠杆菌yhcb的22个氨基酸的膜锚定、以及在位置76、94、131、231、284、383、390、468和499的9个点突变(相对于srko野生型)。图23b，显示了针对野生型srko(seqidno:108)的vo0(seqidno:109)、vo1(seqidno:110)和vo2(seqidno:111)中的点突变(为了方便，所有都用野生型srko的n端显示)。发明详述本发明在各个方面提供了在离体或在细胞系统中用于制备含氧的萜烯或类萜的方法。本发明进一步提供了用于这些方法的工程化的或修饰的酶、多核苷酸和宿主细胞。本发明在各种实施方案中涉及使用srko酶生产诺卡酮的方法。令人惊奇的是，发现srko酶可用于催化倍半萜烯氧化(例如，朱栾倍半萜氧化成诺特卡醇和诺卡酮)。如本文所用，srko是指具有登录号aaq63464.1(seqidno:37)的对映-贝壳杉烯氧化酶cyp701a5[甜菊]。srko和其对双萜(尤其是贝壳杉烯)的活性是已知的并且描述于，例如，us2012/0164678，其据此通过引用整体并入本文。它是细胞色素p450酶(cyp450)的cyp70家族的成员。经修饰以在大肠杆菌中表达的srko序列显示为seqidno:38。如本文所示，srko对于倍半萜烯底物(例如，朱栾倍半萜)有活性，生产诺特卡醇和诺卡酮，它们是有价值的类萜化合物。这些氧合活性和产物谱(例如，增加的诺卡酮的产量)可以通过使用本文详细描述的工艺(和通过计算机模型(insilicomodels)辅助)诱变srko来进一步细化。如本文所用，术语“srko衍生物”或“工程化的srko”是指与srko具有实质性结构和/或序列同一性并催化倍半萜烯支架(诸如，朱栾倍半萜)氧合的氨基酸序列。经工程化用于朱栾倍半萜的氧合的srko酶在本文中也称为“朱栾倍半萜氧化酶”或“vo”酶。通常，衍生物包含具有至少一个突变的srko的突变形式，该突变增加用于朱栾倍半萜底物或用于诺卡酮和/或其它产物的生产的酶的活性。在表2中提供了一些srko突变。一些这样的另外的srko突变提供在表6中。术语“接触”是指体内通过相关蛋白产物(例如，倍半萜烯合成酶和cyp450)在宿主细胞中的共表达，或通过向表达srko或其衍生物的宿主细胞添加或供给感兴趣的底物，或体外(或“离体”)通过将倍半萜烯底物添加到纯化的p450酶或细胞提取物或含有其的部分纯化的提取物中，来将组分物理地聚集在一起。术语体外和离体是指无细胞系统，并且可以在反应管或孔中进行。如本文所用，“萜烯”是具有简单统一特征的大型且不同类别的烃，尽管它们具有结构多样性。根据“异戊二烯规则”，所有萜烯由异戊二烯(c5)单元组成。这个事实被用于根据这种单元的数量的合理分类。单萜包含2个异戊二烯单元并被分类为(c10)萜烯，倍半萜烯包含3个异戊二烯单元并被分类为(c15)萜烯，二萜包含4个异戊二烯单元并被分类为(c20)萜烯、二倍半萜(c25)、三萜(c30)和橡胶(c5)n。它们作为具有醇、醚、酯、醛或酮基团的无环或单环至五环的衍生物(所谓的“类萜化合物”)在生物体中，特别是在高等植物中各处存在，并且是个别类型的植物的特征。萜烯诸如单萜(c10)、倍半萜烯(c15)和二萜(c20)，通过称为萜烯(类萜化合物)合成酶的非常大的一组酶的作用，分别源自异戊基二磷酸底物、香叶基焦磷酸(gpp)、法尼基焦磷酸(fpp)和香叶基香叶基焦磷酸(ggpp)。这些酶通常被称为萜烯环化酶，因为反应的产物被环化成各种单萜、倍半萜烯和二萜碳骨架产物。许多所得碳骨架通过细胞色素p450水解酶进行亚序列氧合，以产生衍生物的大家族。畅销的风味物和芳香物的技术合成可以从萜烯开始，萜烯也可以用作染料和清漆的优异的溶剂或稀释剂。使用萜烯的天然的或合成的树脂，并且维生素和杀虫剂的许多药物合成也从萜烯开始。如本文所用，术语“萜烯”或“倍半萜烯”(例如)包括相应的类萜或类倍半萜烯化合物。如本文所用，术语“含氧的倍半萜烯”是指具有一个或多个氧合事件，产生相应的醇、醛、羧酸和/或酮的倍半萜烯支架。如本文所用，术语“mep途径”是指(2-c-甲基-d-赤藓醇4-磷酸)途径，也称为mep/doxp(2-c-甲基-d-赤藓醇4-磷酸/l-脱氧-d-木酮糖5-磷酸)途径或非甲羟戊酸途径或甲羟戊酸非依赖途径。在mep途径中，丙酮酸和d-甘油醛-3-磷酸通过一系列反应转化为ipp和dmapp。该途径通常涉及以下酶的作用：1-脱氧-d-木酮糖-5-磷酸合成酶(dxs)、1-脱氧-d-木酮糖-5-磷酸还原异构酶(ispc)、4-二磷酸胞苷-2-c-甲基-d-赤藓醇合成酶(ispd)、4-二磷酸胞苷-2-c-甲基-d-赤藓醇激酶(ispe)、2c-甲基-d-赤藓醇2,4-环二磷酸合成酶(ispf)、1-羟基-2-甲基-2-(e)-丁烯基4-二磷酸合成酶(ispg)和异戊烯基二磷酸异构酶(isph)。mep途径以及构成mep途径的基因和酶描述于us8,512,988中，其据此通过引用整体并入本文。例如，构成mep途径的基因包括dxs、ispc、ispd、ispe、ispf、ispg、isph、idi和ispa。如本文所用，mva途径是指将乙酰辅酶a转化为ipp的生物合成途径。甲羟戊酸途径通常包括催化以下步骤的酶：(a)将两分子的乙酰辅酶a缩合成乙酰乙酰辅酶a(例如，通过乙酰乙酰辅酶a硫解酶的作用)；(b)将乙酰乙酰辅酶a与乙酰辅酶a缩合以形成羟甲基戊二酰辅酶a(hmg-coa)(例如，通过hmg-coa合成酶(hmgs)的作用)；(c)将hmg-coa转化为甲羟戊酸(例如，通过hmg-coa还原酶(hmgr)的作用)；(d)将甲羟戊酸磷酸化成甲羟戊酸5-磷酸(例如，通过甲羟戊酸激酶(mk)的作用)；(e)将甲羟戊酸5-磷酸转化为甲羟戊酸5-焦磷酸(例如，通过磷酸甲羟戊酸激酶(pmk)的作用)；和(f)将甲羟戊酸5-焦磷酸转化成异戊烯焦磷酸(例如，通过甲羟戊酸焦磷酸脱羧酶(mpd)的作用)。mva途径以及构成mep途径的基因和酶描述于us7,667,017中，其据此通过引用整体并入本文。如本文所用，术语“细胞色素p450还原酶配偶体”或“cpr配偶体”是指能够再生用于氧化化学的感兴趣的细胞色素p450氧化酶(例如，srko)的辅因子组分的细胞色素p450还原酶。例如，srcpr是srko的天然的cpr配偶体。在一些实施方案中，cpr配偶体不是srko的天然的cpr配偶体。在采用体内生产含氧的倍半萜烯的一些实施方案中，srko和srcpr共表达为分离蛋白，或在一些实施方案中表达为融合蛋白。核苷酸和氨基酸序列的相似性，即序列同一性的百分比，可以通过序列比对来确定。这样的比对可以用几种本领域已知的算法进行，诸如用karlin和altschul的数学算法(karlin&altschul(1993)proc.natl.acad.sci.usa90:5873-5877)、用hmmalign(hmmerpackage,http://hmmer.wustl.edu/)或用clustal算法(thompson，j.d.,higgins,d.g.&gibson,t.j.(1994)nucleicacidsres.22,4673-80)。序列同一性的等级(序列匹配)可以使用例如blast、blat或blastz(或blastx)来计算。将类似的算法并入altschul等人(1990)j.mol.biol.215：403-410的blastn和blastp程序中。blast多核苷酸搜索可以用blastn程序进行，得分＝100，字长＝12。blast蛋白搜索可以用blastp程序进行，得分＝50，字长＝3。为了获得用于比较目的的空位比对，使用gappedblast，如altschul等(1997)nucleicacidsres.25：3389-3402中所描述。当使用blast和gappedblast程序时，使用相应程序的默认参数。序列匹配分析可以通过已建立的同源性作图技术如shuffle-lagan(brudnom.，bioinformatics2003b，19增刊1:154-162)或markov随机场来补充。“保守取代”可以例如基于所涉及的氨基酸残基的极性、电荷、大小、溶解度、疏水性、亲水性和/或两亲性中的相似性进行。20种天然存在的氨基酸可以分为以下六种标准氨基酸组：(1)疏水性：met、ala、val、leu、ile；(2)中性亲水性：cys、ser、thr；asn、gin；(3)酸性：asp、glu；(4)碱性：his、lys、arg；(5)影响链取向的残基：gly、pro；和(6)芳香性：trp、tyr、phe。如本文所用，“保守取代”定义为氨基酸与上文所示的六种标准氨基酸组的相同组内所列的另一氨基酸的交换。例如，asp被glu交换在如此修饰的多肽中保留一个负电荷。此外，甘氨酸和脯氨酸可以基于它们破坏α-螺旋的能力彼此替换。上述六组内的一些优选的保守取代是以下亚组内的交换：(i)ala、val、leu和he；(ii)ser和thr；(ii)asn和gin；(iv)lys和arg；和(v)tyr和phe。如本文所用，“非保守性取代”或“非保守性氨基酸交换”定义为氨基酸被上述六个标准氨基酸组(1)至(6)的不同组中所列的另一氨基酸交换。一方面，本发明提供了用于制备倍半萜烯的含氧产物的方法。在各种实施方案中，倍半萜烯底物是(或主要的倍半萜烯底物是)朱栾倍半萜、大根香叶烯(a、b、c、d或e)、法尼烯、法尼醇、诺特卡醇、广藿香醇、杜松烯、雪松醇、蛇麻烯、长叶烯和/或佛手柑油烯、β-衣兰烯、β-檀香醇、β-檀香烯、α-檀香烯、α-檀香醇、β-香根酮、a-香根酮、客烯醇、红没药烯、β-丁香烯、长叶烯、α-甜橙醛；α-红没药醇、(-)-β-可巴烯、(-)-α-可巴烯、4(z),7(z)-癸二烯醛、雪松醇、雪松烯、雪松醇、愈创木醇、(-)-6,9-愈创木二烯、布藜醇、愈创木醇、喇叭烯、喇叭茶醇、香樟烯和α-佛手柑油烯。在一些实施方案中，主要的倍半萜烯底物是朱栾倍半萜，并且主要的含氧产物是诺卡酮和/或诺特卡醇。在上下文中，术语“主要的”是指特定的倍半萜烯单独地以高于所有其它萜烯或类萜物质的水平存在。在一些实施方案中，主要的倍半萜烯(底物或反应后的含氧的产物)构成组合物的至少25％、至少40％、至少50％或至少75％的萜烯或类萜组分。在涉及含氧的倍半萜烯的体内生产的各种实施方案中，从培养基中回收氧合产物，并且可以分级以分离或富集产物的各种组分，诸如诺卡酮。在一些实施方案中，诺卡酮被分离和/或富集，使得其组成倍半萜烯组分的至少约25％、至少约40％、至少约50％、至少约60％、至少约70％、至少约80％或至少约90％(以重量计)，或构成诺特卡醇和诺卡酮的总量的至少约25％、至少约40％、至少约50％、至少约60％、至少约70％、至少约80％、至少约90％或约100％(以重量计)。在各种实施方案中，本发明包括使倍半萜烯与萜烯氧化性p450酶或其衍生物接触。接触可以在宿主细胞或无细胞系统中进行。用于氧化的底物(例如，倍半萜烯)可以由细胞产生(例如，通过经mep或mva途径的代谢通量)，或供给到表达p450酶的宿主细胞。含氧的产物可以回收，或作为在细胞系统或无细胞系统中进一步化学转化的底物。下表1提供了示例性p450酶的列表。虽然在某些实施方案中，本发明涉及使用以下p450酶(任选工程化以增加朱栾倍半萜氧合为诺卡酮和/或诺特卡醇)，但根据本公开优选的酶是srko。通过根据本公开的这些反应获得的示例性含氧的倍半萜烯产物显示在表4中。表1在各种实施方案中，方法包括使倍半萜烯与包含甜菊贝壳杉烯氧化酶(srko)或其衍生物的蛋白质接触。在一些实施方案中，srko在如下所述的宿主细胞中表达，或在无细胞系统中提供。例如，用于用p450酶氧化萜烯的某些体外和体内系统公开于据此通过引用并入本文的us7,211,420中。mcdougledr,palariaa,magnettae,melingdd,dasa.functionalstudiesofn-terminallymodifiedcyp2j2epoxygenaseinmodellipidbilayers,proteinsci.201322：964-79；luthra,a.,gregory,m.,grinkova,y.v.,denisov,i.g.,sligar,s.g.(2013)"nanodiscsinthestudiesofmembrane-boundcytochromep450enzymes."methodsmol.biol.,987,115-127)。在一些实施方案中，srko衍生物包含相对于srko(seqidno:37)或相对于在n端修饰用于大肠杆菌中功能性表达的srko酶(seqidno:38或55)具有约1至约50个独立选自替换、缺失或插入的突变的氨基酸序列。在各种实施方案中，突变或突变的组合增强用于朱栾倍半萜的氧合的酶的活性，诸如诺卡酮的产量。本文所述的蛋白建模可用于指导srko序列中的这种替换、缺失或插入。例如，可以使用p45017a1的坐标建立srko氨基酸序列的结构模型。如本文所证明的，这种同源模型可用于指导用于朱栾倍半萜氧合的srko的改善。因此，在各种实施方案中，srko衍生物相对于srko(seqidno:37、38或55)可具有约1至约45个突变、约1至约40个突变、约1至约35个突变、约1至约30个突变、约1至约25个突变、约1至约20个突变、约1至约15个突变、约1至约10个突变或约1至约5个突变。在各种实施方案中，srko包含相对于seqidno:37、38或55具有至少5或至少10个突变但不超过约20或30个突变的序列。在各种实施方案中，srko衍生物相对于srko(seqidno:37、-38或55)可具有约1个突变、约2个突变、约3个突变、约4个突变、约5个突变、约6个突变、约7个突变、约8个突变、约9个突变、约10个突变、约11个突变、约12个突变、约13个突变、约14个突变、约15个突变、约16个突变、约17个突变、约18个突变、约19个突变、约20个突变、约21个突变、约22个突变、约23个突变、约24个突变、约25个突变、约26个突变、约27个突变、约28个突变、约29个突变、约30个突变、约31个突变、约32个突变、约33个突变、约34个突变、约35个突变、约36个突变、约37个突变、约38个突变、约39个突变、约40个突变、约41个突变、约42个突变、约43个突变、约44个突变、约45个突变、约46个突变、约47个突变、约48个突变、约49个突变或约50个突变。seqidno:37和本文公开的其它wt酶可以任选地包含野生型中不存在的位置2的ala。在这些或其他实施方案中，srko衍生物可以包含与srko(seqidno:37、38或55)具有至少约50％序列同一性、至少约55％序列同一性、至少约60％序列同一性、至少约65％序列同一性、至少约70％序列同一性、至少约75％序列同一性、至少约80％序列同一性、至少约85％序列同一性、或至少90％序列同一性、或至少91％序列同一性、或至少92％序列同一性、或至少93％序列同一性、或至少94％序列同一性、或至少95％序列同一性、或至少96％序列同一性、或至少97％序列同一性、或至少98％同一性、或至少99％序列同一性的氨基酸序列。在各种实施方案中，srko衍生物对于朱栾倍半萜的氧合活性比野生型酶高，诸如在与朱栾倍半萜底物接触时比野生型酶(seqidno:37)或经修饰用于大肠杆菌中的功能性表达的野生型酶有更高产量的含氧的油。例如，srko衍生物可以包含与srko(seqidno:37、38或55)具有至少：约50％同一性、约51％同一性、约52％同一性、约53％同一性、约54％同一性、约55％同一性、约56％同一性、约57％同一性、约58％同一性、约59％同一性、约60％同一性、约61％同一性、约62％同一性、约63％同一性、约64％同一性、约65％同一性、约66％同一性、约67％同一性、约68％同一性、约69％同一性、约70％同一性、约71％同一性、约72％同一性、约73％同一性、约74％同一性、约75％同一性、约76％同一性、约77％同一性、约78％同一性、约79％同一性、约80％同一性、约81％同一性、约82％同一性、约83％同一性、约84％同一性、约85％同一性、约86％同一性、约87％同一性、约88％同一性、约89％同一性、约90％同一性、约91％序列同一性、约92％序列同一性、约93％序列同一性、约94％序列同一性、约95％序列同一性、约96％序列同一性、约97％序列同一性、约98％序列同一性或约99％序列同一性的氨基酸序列。在一些实施方案中，选择突变体用于增加含氧的朱栾倍半萜(诸如诺卡酮)的产量。例如，相对于seqidno:37，srko衍生物可以在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个、两个、三个、四个或更多个突变。例如，在一些实施方案中，srko是包含相对于seqidno:37具有一个或多个(例如，2、3、4个或全部)选自r76k、m94v、t131q、f231l、h284q、r383k、i390l、t468i和t499n的突变的氨基酸序列的衍生物。在一些实施方案中，srko衍生物包含选自seqidno:55-61、104或105的氨基酸序列，其根据本公开被工程化以改善用于朱栾倍半萜氧合的活性(例如，诺卡酮的产量)。在一些实施方案中，衍生物包含相对于选自seqidno:55-61、104和105的序列具有1至20、或1至10、或1至5个突变的氨基酸序列，附带条件是氨基酸序列相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个或多个突变，或附带条件是srko衍生物包含相对于seqidno:37具有选自r76k、m94v、t131q、f231l、h284q、r383k、i390l、t468i和t499n的1个、2个、3个或更多个(或全部)突变的氨基酸序列。在一些实施方案中，本发明提供了编码上述srko衍生物的重组多核苷酸，其可以被插入用于表达和任选纯化的表达载体中。在一些实施方案中，将多核苷酸并入产生朱栾倍半萜的细胞(诸如产生朱栾倍半萜的大肠杆菌细胞)的基因组中。各种实施方案中的srko或衍生物具有朱栾倍半萜氧化酶活性。用于测定和定量朱栾倍半萜氧化酶活性的检测在本文中被描述并且是本领域已知的。检测包括在产生朱栾倍半萜的细胞(例如，表达fpps和朱栾倍半萜合成酶的大肠杆菌)中表达srko(或衍生物)，以及从水性反应介质中提取氧化的油。类萜产物的谱可以通过gc/ms定量测定。测试对朱栾倍半萜氧化酶活性的影响的srko的各种突变列于表2或表6中。因此，在各种实施方案中，srko可以具有至少约1个、至少约2个、至少约3个、至少约4个、至少约5个、至少约6个、至少约7个、至少约8个、至少约9个、或至少约10个选自表2或表6的突变。在一些实施方案中，srko衍生物是修饰的srko多肽，其包含与根据seqidno:37的野生型蛋白相比具有多至25个突变的氨基酸序列(或经修饰用于在大肠杆菌中表达的其对应物，并且包括至少与v375f、v375a、v375m、m120l、m120i、m120v、f129l、f129i、l114v、l114f和v121a(根据seqidno:38编号)中的至少任一个或多个组合的替换i310v、v375i或t487n，并任选地包含支持大肠杆菌中功能性表达的前导序列(如seqidno:38所示)。表2.1根据野生型srko(seqidno:37)和8rp-t20srko(seqidno:38)编号的一些被测试的甜菊贝壳杉烯氧化酶突变的概述。表2.2：在vo1背景(n22-yhcb-t30-vo1，seqidno:110)中评估以下突变体。位置维持seqidno:37的编号。srko可在各种宿主细胞中表达，用于重组蛋白生产或用于倍半萜烯(例如，朱栾倍半萜)氧化。例如，宿主细胞包括us8,512,988中描述的那些，其据此通过引用整体并入本文。宿主细胞可以是原核或真核细胞。在一些实施方案中，细胞是细菌细胞，诸如埃希氏菌属(escherichiaspp.)、链霉菌属(streptomycesspp.)、发酵单胞菌属(zymonasspp.)、醋酸杆菌属(acetobacterspp.)、枸橼酸杆菌属(citrobacterspp.)、集胞藻属(synechocystisspp.)、根瘤菌属(rhizobiumspp.)、梭菌属(clostridiumspp.)、棒状杆菌属(corynebacteriumspp.)、链球菌属(streptococcusspp.)、黄单胞菌属(xanthomonasspp.)、乳杆菌属(lactobacillusspp.)、乳球菌属(lactococcusspp.)、芽孢杆菌属(bacillusspp.)、产碱杆菌属(alcaligenesspp.)、假单胞菌属(pseudomonasspp.)、气单胞菌属(aeromonasspp.)、固氮菌属(azotobacterspp.)、丛毛单胞菌属(comamonasspp.)、分支杆菌属(mycobacteriumspp.)、红球菌属(rhodococcusspp.)、葡萄糖酸菌属(gluconobacterspp.)、青枯菌属(ralstoniaspp.)、嗜酸硫杆菌属(acidithiobacillusspp.)、小月菌属(microlunatusspp.)、地杆菌属(geobacterspp.)、地芽孢杆菌属(geobacillusspp.)、节杆菌属(arthrobacterspp.)、黄杆菌属(flavobacteriumspp.)、沙雷氏菌属(serratiaspp.)、糖多孢菌属(saccharopolysporaspp.)、栖热菌属(thermusspp.)、寡养单胞菌属(stenotrophomonasspp.)、色杆菌属(chromobacteriumspp.)、中华根瘤菌属(sinorhizobiumspp.)、糖多孢菌属(saccharopolysporaspp.)、土壤杆菌属(agrobacteriumspp.)和泛菌属(pantoeaspp.)。细菌细胞可以是革兰氏阴性细胞诸如大肠杆菌(e.coli)细胞、或革兰氏阳性细胞诸如芽孢杆菌属的种类。在其他实施方案中，细胞是真菌细胞，诸如酵母细胞，诸如，例如，酵母属、裂殖酵母属(schizosaccharomycesspp.)、毕赤酵母属、法夫酵母属(paffiaspp.)、克鲁维酵母属(kluyveromycesspp.)、念珠菌属(candidaspp.)、踝节菌属(talaromycesspp.)、酒香酵母属(brettanomycesspp.)、管囊酵母属(pachysolenspp.)、德巴利酵母属(debaryomycesspp.)、耶氏酵母属和工业多倍体酵母菌株。在一个实施方案中，宿主细胞是选自大肠杆菌、枯草芽孢杆菌或恶臭假单胞菌中的细菌。在一个实施方案中，宿主细胞是酵母，并且可以是酵母属、毕赤酵母属或耶氏酵母属的种类，包括酿酒酵母、巴斯德毕赤酵母和解脂耶氏酵母。在一些实施方案中，宿主细胞产生异戊基焦磷酸(ipp)，其用作合成倍半萜烯的底物。在一些实施方案中，通过内源或异源的甲基赤藓糖醇磷酸(mep)或甲羟戊酸(mva)途径的代谢通量(例如，用供给至细胞的碳源开始)产生ipp。在某些实施方案中，可以通过异源酶的表达或途径中某些酶的复制来增强mep或mva途径。mep(2-c-甲基-d-赤藓醇4-磷酸)途径，也称为mep/doxp(2-c-甲基-d-赤藓醇4-磷酸/1-脱氧-d-木酮糖5-磷酸)途径或非甲羟戊酸途径或甲羟戊酸非依赖性途径，是指将甘油醛-3-磷酸和丙酮酸转化为ipp和dmapp的途径。该途径通常涉及以下酶的作用：1-脱氧-d-木酮糖-5-磷酸合成酶(dxs)、1-脱氧-d-木酮糖-5-磷酸还原异构酶(ispc)、4-二磷酸胞苷-2-c-甲基-d-赤藓糖醇合成酶(ispd)、4-二磷酸胞苷-2-c-甲基-d-赤藓糖醇激酶(ispe)、2c-甲基-d-赤藓醇2,4-环二磷酸合成酶(ispf)、1-羟基-2-甲基-2-(e)-丁烯基4-二磷酸合成酶(ispg)和异戊烯基二磷酸异构酶(isph)。mep途径以及构成mep途径的基因和酶描述于us8,512,988中，其据此通过引用整体并入本文。例如，构成mep途径的基因包括dxs、ispc、ispd、ispe、ispf、ispg、isph、idi和ispa。在一些实施方案中，倍半萜烯至少部分地通过经mep途径的代谢通量产生，并且其中宿主细胞具有dxs、ispd、ispf和/或idi基因的至少一个另外的拷贝(例如，dxs和idi；或dxs、ispd、ispf和/或idi)。mva途径是指将乙酰辅酶a转化为ipp的生物合成途径。甲羟戊酸途径通常包括催化以下步骤的酶：(a)将两分子乙酰辅酶a缩合成乙酰乙酰辅酶a(例如，通过乙酰乙酰辅酶a硫解酶的作用)；(b)将乙酰乙酰辅酶a与乙酰辅酶a缩合以形成羟甲基戊二酰辅酶a(hmg-coa)(例如，通过hmg-coa合成酶(hmgs)的作用)；(c)将hmg-coa转化为甲羟戊酸(例如，通过hmg-coa还原酶(hmgr)的作用)；(d)将甲羟戊酸磷酸化成甲羟戊酸5-磷酸(例如，通过甲羟戊酸激酶(mk)的作用)；(e)将甲羟戊酸5-磷酸转化为甲羟戊酸5-焦磷酸(例如，通过磷酸甲羟戊酸激酶(pmk)的作用)；和(f)将甲羟戊酸5-焦磷酸转化为异戊烯焦磷酸(例如，通过甲羟戊酸焦磷酸脱羧酶(mpd)的作用)。mva途径以及构成mep途径的基因和酶描述于us7,667,017中，其据此通过引用整体并入本文。在一些实施方案中，宿主细胞表达法尼基焦磷酸合成酶(fpps)，其从ipp或dmapp产生法尼基焦磷酸。如图1所示，法尼基焦磷酸是用于生产朱栾倍半萜的中间体。示例性的法尼基焦磷酸合成酶是酿酒酵母的erg20(ncbi登录号p08524)和大肠杆菌ispa。各种其他原核、酵母、植物和哺乳动物fpps酶是已知的，并且可以根据这方面使用。宿主细胞可以进一步表达异源倍半萜烯合成酶(诸如朱栾倍半萜合成酶)以产生所需的倍半萜烯。已知几种朱栾倍半萜合成酶，包括来自葡萄柚或来自甜橙(citrussinensis)的朱栾倍半萜合成酶。甜橙vs(例如，aaq04608.1)及其各种衍生物描述于us2012/0246767中，其据此通过引用并入本文。例如，本发明可以采用甜橙朱栾倍半萜合成酶的氨基酸序列(seqidno:12)，或相对于野生型氨基酸序列(seqidno:12)具有1至30个突变或1至20个或1至10个突变的衍生物。这样的序列与野生型序列(seqidno:12)可以具有至少60％的序列同一性、至少70％的序列同一性、至少80％的序列同一性、至少90％的序列同一性、至少95％的序列同一性、或至少约96％、约97％、约98％或约99％的序列同一性。进一步地，licker等(phytochemistry(2004)65:2649-2659)描述了来自葡萄(vvvs)(seqidno:1)的朱栾倍半萜合成酶。在一个实施方案中，包括vvvs的氨基酸序列的朱栾倍半萜合成酶或其工程化的衍生物可用于本发明。各种倍半萜烯合成酶诸如朱栾倍半萜合成酶是已知的，并且描述于例如us2012/0107893、us2012/0246767和us7,273,735中，其据此通过引用整体并入本文。例如，在一些实施方案中，朱栾倍半萜合成酶是vvvs衍生物，其包含相对于vvvs(seqidno:1)具有独立地选自替换、缺失或插入的约1至约40个突变、约1至约35个突变、约1至约30个突变、约1至约25个突变、约1至约20个突变、约1至约15个突变、或约1至约10个突变的氨基酸序列。例如，vvvs衍生物可以包含相对于seqidno:1具有至少约5个或至少约10个，但少于约30个或约20个突变的氨基酸序列。在各种实施方案中，vvvs衍生物包含相对于vvvs(seqidno:1)具有约1个突变、约2个突变、约3个突变、约4个突变、约5个突变、约6个突变、约7个突变、约8个突变、约9个突变、约10个突变、约11个突变、约12个突变、约13个突变、约14个突变、约15个突变、约16个突变、约17个突变、约18个突变、约19个突变、约20个突变、约21个突变、约22个突变、约23个突变、约24个突变、约25个突变、约26个突变、约27个突变、约28个突变、约29个突变、约30个突变、约31个突变、约32个突变、约33个突变、约34个突变、约35个突变、约36个突变、约37个突变、约38个突变、约39个突变或约40个突变的氨基酸序列。这样的序列可以与seqidno:1具有至少60％的序列同一性、至少70％的序列同一性、至少80％的序列同一性、至少90％的序列同一性、至少95％的序列同一性、或至少约96％、约97％、约98％或约99％的序列同一性。vvvs的示例性突变示于表3中。基于作为模板的5-非手性-马兜铃烯合成酶晶体结构(pdb：5eat)的葡萄朱栾倍半萜合成酶(vvvs)的同源性模型可以指导突变。表3.1相对于野生型(seqidno:1)的葡萄朱栾倍半萜合成酶突变的概述表3.2：在vv2m5背景(seqidno:9)中评估的突变的概述。表3.3：在vs2背景(seqidno:11)中评估的突变的概述。因此，在各种实施方案中，工程化的vvvs可以具有选自表3的至少约1个突变、约2个突变、约3个突变、约4个突变、约5个突变、约6个突变、约7个突变、约8个突变、约9个突变、约10个突变、约11个突变、约12个突变、约13个突变、约14个突变、约15个突变、约16个突变、约17个突变、约18个突变、约19个突变、约20个突变、约21个突变、约22个突变、约23个突变、约24个突变、约25个突变、约26个突变、约27个突变、约28个突变、约29个突变、约30个突变、约31个突变、约32个突变、约33个突变、约34个突变、约35个突变、约36个突变、约37个突变、约38个突变、约39个突变或约40个突变。图3中进一步描述了示例性的重组朱栾倍半萜合成酶vv1m1(seqidno:3)、vv2m1(seqidno:5)、vv1m5(seqidno:7)、vv2m5(seqidno:9)和vs2(seqidno:11)，包括图3b中的比对。在某些方面，本发明提供了多核苷酸，所述多核苷酸包含编码经修饰用于增加如上所述的朱栾倍半萜的表达的朱栾倍半萜合成酶的核苷酸序列。这样的多核苷酸可以在宿主细胞中表达，在染色体外元件诸如质粒上，或可以染色体整合。在各种实施方案中，srko与p450还原酶一起表达以再生酶，或者，srko或衍生物与p450还原酶表达为嵌合p450酶。由于细菌平台的固有限制，诸如缺乏电子转移机制和细胞色素p450还原酶，以及由于缺乏内质网导致的p450酶的膜信号模块的翻译不相容性，细胞色素p450的功能性表达已被认为是具有挑战性的。因此，在一些实施方案中，srko表达为具有细胞色素p450还原酶配偶体的融合蛋白。细胞色素p450还原酶是在内质网中发现的膜蛋白。它催化吡啶核苷酸脱水和电子转移到膜结合的细胞色素p450。在人、植物、其它哺乳动物和昆虫中发现了类似结构的同功酶。示例性的p450还原酶配偶体包括，例如，甜菊(sr)cpr(seqidno:62和63)、甜菊(sr)cpr1(seqidno:76和77)、拟南芥(at)cpr(seqidno:64和65)、红豆杉(tc)cpr(seqidno:66和67)、青蒿(aa)cpr(seqidno:68和69)、拟南芥(at)cpr1(seqidno:70和71)、拟南芥(at)cpr2(seqidno:72和73)、拟南芥(at)r2(seqidno:74和75)、甜菊(sr)cpr2(seqidno:78和79)；甜菊(sr)cpr3(seqidno:80和81)；香叶天竺葵(pg)cpr(seqidno:82和83)。在一些实施方案中，这些p450中的任何一个都可以被衍生化，例如，以引入1至约20个突变或约1至约10个突变。图6b显示了拟南芥和青蒿cpr序列(seqidno:72、74、68、64和70)的氨基酸序列的比对。图6c显示了甜菊cpr序列(seqidno:78、80、62和76)的比对。图6d显示了8个cpr氨基酸序列(seqidno:74、72、82、68、80、62、78和76)的比对。p450融合蛋白的工程化公开于例如us2012/0107893和us2012/0164678中，其据此通过引用整体并入本文。在某些实施方案中，srko通过连接子与细胞色素p450还原酶配偶体融合。示例性的连接子序列主要是丝氨酸、甘氨酸和/或丙氨酸，以及任选地1至5个带电荷的氨基酸(诸如赖氨酸或精氨酸)，所述示例性连接子序列包括例如，gsg、gsggggs(seqidno:113)、gsgeaaak(seqidno:114)、gsgeaaakeaaak(seqidno:115)、gsgmgsssn(seqidno:116)和gstgs(seqidno:117)。连接子通常是柔性的，并且包含不超过1个、2个或3个疏水残基，并且通常长度为3至50个氨基酸，诸如长度为3至20个氨基酸。在其他实施方案中，p450还原酶在宿主细胞中单独表达，并且在一些实施方案中可以在与srko相同的操纵子中表达。在一些实施方案中，p450还原酶在宿主细胞中单独表达，并且基因任选地整合到基因组中或从质粒表达。在某些实施方案中，p450酶的n端可以被工程化以增加它们的功能表达。膜结合p450的n端在酶表达、膜缔合和底物接近中起重要作用。据报道，在p450的n端使用稀有密码子显着改善p450的表达水平。进一步地，因为大多数植物p450酶是膜结合的，并且疏水底物被认为通过在p450和膜之间动态建立的通道进入酶，n端工程化可以影响膜和p450的缔合，并因此底物接近酶。因此，在一个实施方案中，srko的n端工程化产生srko衍生物，srko衍生物在宿主系统诸如大肠杆菌或酵母中维持或显示增强的朱栾倍半萜氧化酶活性。示例性的n端序列是malllavf(seqidno:112)，其他示例性序列包括主要为疏水性的4至20个氨基酸(诸如4至15个氨基酸，或4至10个氨基酸，或约8个氨基酸)的序列，例如，优选由选自亮氨酸、缬氨酸、丙氨酸、异亮氨酸和苯丙氨酸的(至少50％或至少75％)氨基酸构成。在一些实施方案中，srko是缺失其n端跨膜区的至少一部分并且添加来自大肠杆菌yhcb或其衍生物的内膜跨膜结构域的衍生物。在这些实施方案中，p450酶与大肠杆菌内膜具有更稳定和/或有成效的缔合，这减少了膜缔合的p450酶的表达诱导的细胞应激。在一些实施方案中，srko是缺失其n端跨膜结构域的15至35个氨基酸并且添加来自大肠杆菌yhcb或其衍生物的跨膜结构域的15至25个氨基酸的衍生物。在一些实施方案中，衍生物的n端跨膜结构域包含氨基酸序列maweyaliglvvgiiigava(seqid_no:118)或相对于seqidno:118具有1至10个或1至5个氨基酸突变的氨基酸序列。在一些实施方案中，宿主细胞进一步表达一种或多种将产物转换为诺卡酮的酶。例如，宿主细胞可以表达从诺特卡醇产生诺卡酮的醇脱氢酶，其实例包括红串红球菌cdh(seqidno:84)、甜橙dh(seqidno:86)、甜橙dh1(seqidno:88)、甜橙dh2(seqidno:90)、甜橙dh3(seqidno:92)、葡萄dh(seqidno:94)、葡萄dh1(seqidno:96)、甜橙aba2(seqidno:98)、短柄草dh(seqidno:100)和红球姜sdr(seqidno:102)。醇脱氢酶可以包含与本段落中描述的一种或多种酶具有至少70％、至少80％或至少90％序列同一性的并具有将诺特卡醇转化为诺卡酮的活性的氨基酸序列。倍半萜烯(例如，朱栾倍半萜及其含氧产物)可以作为大肠杆菌中非甲羟戊酸途径的生物合成产物产生，其包括两个模块：形成异戊烯焦磷酸(ipp)的天然上游途径和形成类萜的异源下游途径。可以采用代谢途径工程化的多变量模块方法来优化工程化的大肠杆菌中倍半萜烯的生产。多变量模块途径工程化的方法基于系统多变量搜索，以识别最佳平衡两个途径模块的条件，从而使抑制性中间体的积累和通量转移至副产物减至最小。wo2011/060057、us2011/0189717、us2012/107893和us8512988(其各自据此通过引用并入本文)描述了通过控制参与上游途径和下游途径的基因或蛋白的表达来优化细胞中类萜生产的方法和组合物。这可以通过将酶途径分组为两个模块来实现：上游(mep)途径模块(例如，包括mep途径的一个或多个基因)和倍半萜烯生产的下游异源途径。使用这种基本构型，就其对萜烯和类萜(例如，倍半萜烯)生产的影响来评估参数，诸如质粒拷贝数对细胞生理学的影响、表达盒中的基因顺序和启动子强度、以及染色体整合。因此可以在模块化方法中调节mep途径内的基因表达。如本文所用，通过模块化方法调节是指多个基因一起调节。通过实例，mep途径内的多个基因可以在dna的连续区域诸如操纵子上重组表达。应当理解，与本发明的方面一致，mep途径内的基因模块可以以任何顺序包含mep途径内的任何基因。在一些实施方案中，mep途径内的基因是以下之一：dxs、ispc、ispd、ispe、ispf、ispg、isph、idi、ispa或ispb。mep途径内的基因模块的非限制性实例是包含基因dxs、idi、ispd和ispf的模块，并且称为dxs-idi-ispdf。可以通过本领域普通技术人员已知的方法实现基因和/或蛋白(包括诸如dxs-idi-ispdf操纵子和fpps-vs操纵子的模块)表达的操作。例如，可以通过选择具有不同强度的启动子(诸如诱导型启动子)来调节基因或操纵子的表达。启动子的几个非限制性实例包括trc、t5和t7。另外，可以通过操作细胞中基因或操纵子的拷贝数来调节基因或操纵子的表达。mep途径内的一种或多种基因和/或蛋白的表达可以被上调和/或下调。在某些实施方案中，mep途径内的一种或多种基因和/或蛋白的上调可以与mep途径内的一种或多种基因和/或蛋白的下调组合。通过实例，在一些实施方案中，过表达非甲羟戊酸(mep)途径的一种或多种组分的细胞至少部分用于扩增异戊基二磷酸(ipp)和二甲基烯丙基二磷酸(dmapp)，ggpps的底物。在一些实施方案中，非甲羟戊酸(mep)途径的一种或多种组分的过表达通过增加非甲羟戊酸(mep)途径的一种或多种组分的拷贝数来实现。在这方面，诸如通过额外的游离型表达，可以扩增mep途径中限速步骤的组分诸如(dxs、ispd、ispf、idi)的拷贝数。在一些实施方案中，吲哚的生产用作倍半萜烯生产的替代标记，和/或控制培养物中吲哚的积累以增加倍半萜烯的产量。例如，在各种实施方案中，将培养物中吲哚的积累控制到低于约100mg/l、或低于约75mg/l、或低于约50mg/l、或低于约25mg/l、或低于约10mg/l。可以通过使用上述的多元模块化方法平衡蛋白表达和活性来控制吲哚的积累，和/或通过化学方法来控制。在其它方面，本发明提供了制备含有含氧的倍半萜烯(如所述)的产品的方法，其包括将根据上述方法制备和回收的含氧的倍半萜烯掺入消费品或工业产品中。例如，产品可以是风味产品、芳香产品、化妆品、清洁产品、洗涤剂或肥皂，或害虫防治产品(例如驱虫剂)。在一些实施方案中，通过分级(例如分馏)回收和任选富集的含氧的产物是诺卡酮，并且产品是选自饮料、口香糖、糖果或风味添加剂的风味产品，或是驱虫剂。氧化产物可以通过任何合适的方法回收，包括将所需产物分配到有机相中。可以例如通过气相色谱法(例如，gc-ms)测定和/或定量所需产物的产量。可以在间歇或连续生物反应器系统中生产所需产物。产物的生产、回收和/或产物的分析可以如us2012/0246767中所述进行，其据此通过引用整体并入本文。例如，在一些实施方案中，从水性反应介质中提取氧化油，提取可以通过分配到有机相中进行，例如，使用有机溶剂诸如烷烃诸如庚烷，然后分馏。可以通过gc/ms定量测量级分的倍半萜烯和类倍半萜烯组分，然后混合级分以产生用于风味(或其它)应用的所需的含诺卡酮的成分。在其他方面，本发明提供了包含编码本文所述的p450衍生物的核苷酸序列的多核苷酸。在一些实施方案中，多核苷酸可以被密码子优化以在大肠杆菌或酵母中表达。在另一个实例中，多核苷酸可以包含编码srko融合蛋白的核苷酸序列，任选地具有本文所述的p450还原酶配偶体。在其他实施方案中，本发明提供了包含编码本文所述的倍半萜烯合成酶变体的核苷酸序列的多核苷酸，所述多核苷酸同样可以被密码子优化用于在大肠杆菌或酵母中表达。除了编码p450或倍半萜烯合成酶的序列之外，这样的多核苷酸可以进一步包含一个或多个表达控制元件。例如，多核苷酸可以包含一个或多个启动子或转录增强子、核糖体结合位点、转录终止信号和聚腺苷酸化信号作为表达控制元件。多核苷酸可以被插入任何合适的载体中，包括表达载体，并且多核苷酸可以被包含在用于表达的任何合适的宿主细胞中。多核苷酸可以被设计成用于引入任何合适的宿主细胞(包括细菌细胞和酵母细胞)中和/或表达蛋白质，并且可以从质粒表达，或可以被染色体整合。在一些实施方案中，重组核酸分子编码与野生型酶(seqidno:37)相比具有更高的朱栾倍半萜氧化活性的srko衍生物，并具有所述的前导序列，诸如前导序列malllavf(seqidno:117)或源自大肠杆菌yhcb的前导序列。在某些实施方案中，重组核酸分子进一步编码作为操纵子或作为与能够再生srko酶的srko衍生物、srcpr或其衍生物的框内融合。当作为融合蛋白存在时，srko衍生物和srcpr可以通过3至10个氨基酸(例如，5个氨基酸)的连接序列连接。在一些实施方案中，连接序列主要为甘氨酸、丝氨酸和/或丙氨酸，并且可以包含序列gstgs。在其它方面，本发明提供了产生如本文所述的含氧的倍半萜烯的宿主细胞，其表达用于从异戊基焦磷酸(ipp)产生所需含氧的倍半萜烯的所有酶组分。例如，在各种实施方案中，宿主细胞表达法尼基焦磷酸合成酶、倍半萜烯合成酶和srko或其衍生物。ipp可以通过mep和/或mva途径产生，其对于宿主细胞可以是内源性的或通过异源酶的表达或途径中某些酶的复制来修饰。宿主细胞包括本文所述的各种细菌和酵母。在其它方面，本发明提供了通过本文所述的方法和宿主细胞生产的倍半萜烯产物。如本文所公开，srko酶通过产生诺特卡醇并进一步氧化成酮(诺卡酮)，显示出独特的活性，并产生不同的含氧的萜烯产物，包括羟基大根香叶-1(10)5-二烯和依兰烷-3,9(11)二烯-10-过氧化物。此外，测试的其它p450酶，包括先前已知的对朱栾倍半萜底物具有羟化活性的倍半萜烯cyp450或p450，产生一种立体异构体(β-诺特卡醇)和仅少量的酮(诺卡酮)。具体地，其他倍半萜烯cyp450酶产生β-诺特卡醇和羟基朱栾倍半萜作为主要产物，而紫杉醇cyp450酶不产生任何含氧的朱栾倍半萜(表4和图7)。在某些方面，本发明涉及srko衍生物酶。例如，srko衍生物可以包含相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个或多个突变的氨基酸序列。例如，在一些实施方案中，srko是包含相对于seqidno:37具有选自r76k、m94v、t131q、f231l、h284q、r383k、i390l、t468i和t499n的一个或多个(2个、3个、4个或全部)突变的氨基酸序列的衍生物。在一些实施方案中，srko衍生物包含选自seqidno:55-61、104或105的氨基酸序列，其根据本公开被工程化以提高朱栾倍半萜的氧合活性(例如，诺卡酮的产量)。在一些实施方案中，衍生物包含相对于选自seqidno:55-61、104或105的序列具有1至20个突变、或1至10个突变、或1至5个突变的氨基酸序列，附带条件是氨基酸序列相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有1个、2个、3个或更多个突变，或附带条件是srko衍生物包含相对于seqidno:37具有选自r76k、m94v、t131q、f231l、h284q、r383k、i390l、t468i和t499n的1个、2个、3个或更多个(或全部)突变的氨基酸序列。如本文所示，这些突变提高srko朱栾倍半萜氧化活性的水平。在这些或其他实施方案中，srko是缺失其n端跨膜区的至少一部分并添加来自大肠杆菌yhcb或其衍生物的内膜跨膜结构域的衍生物。在一些实施方案中，srko是缺失其n端跨膜结构域的15至35个氨基酸(相对于seqidno:37)并添加来自大肠杆菌yhcb或其衍生物的跨膜结构域的15至25个氨基酸的衍生物。在一些实施方案中，衍生物的n端跨膜结构域包含氨基酸序列maweyaliglvvgiiigava(seqidno:118)或相对于seqidno:118具有1至10个或1至5个氨基酸突变的氨基酸序列。在其它方面，本发明提供了制备经修饰的srko多肽的方法，其中所述方法包括以下步骤：(i)在允许多肽表达的条件下培养表达经修饰的多肽的宿主细胞；和(ii)任选地回收多肽。在其他方面，本发明提供了一种制备含氧的倍半萜烯的方法，包括以下步骤：(i)提供经修饰的srko多肽，(ii)使倍半萜烯与经修饰的srko多肽接触，和(iii)回收所产生的含氧的倍半萜烯。所述方法可以进一步包括提供用于再生srko辅因子(例如，srcpr)的cpr酶。在一些实施方案中，回收含氧的倍半萜烯作为油。在一些实施方案中，倍半萜烯是朱栾倍半萜。在一些实施方案中，含氧的倍半萜烯包括羟基大根香叶-1(10)5-二烯、依兰烷-3,9(11)二烯-10-过氧化物、诺特卡醇和诺卡酮。在一些实施方案中，主要的含氧产物是诺卡酮和/或诺特卡醇。在另一方面，提供了基于p45017a1的结构坐标的srko晶体模型结构(cms)，其具有本文所述的srko或衍生物的氨基酸序列。cms包含萜烯结合口袋结构域(tbd)，tbd包含萜烯结合口袋(tbp)和结合到tbd的萜烯(例如，朱栾倍半萜)。图8a和8b。这种srko晶体模型结构(cms)促进srko衍生物的计算机测试。因此，在其它实施方案中，本发明提供了筛选能够结合tbd的萜烯的方法，其中所述方法包括使用srkocms。在另一方面，本发明提供了筛选能够结合tbp的萜烯的方法，所述方法包括使tbp与测试化合物接触，以及确定所述测试化合物是否结合到所述tbp。在一些实施方案中，所述方法是要筛选可用于调节srko酶的活性的测试化合物(例如，萜烯)。在另一方面，本发明提供了用于预测、模拟或建模萜烯结合结构域(tbd)的分子特征和/或分子相互作用的方法，包括使用计算机模型，所述计算机模型包括使用或描述如上定义的萜烯结合结构域的结构坐标，以提供所述配体结合结构域的图像并任选地显示所述图像。实施例实施例1：生产大肠杆菌菌株的倍半萜烯前体(朱栾倍半萜)的构建产生过表达上游mep途径基因dxs、ispd、ispf和idi的大肠杆菌，其促进通量至支持超过1g/l滴度的异源二类萜产物(3)的类异戊二烯前体异戊基焦磷酸(ipp)。通过用法尼基焦磷酸合成酶(fpps)和倍半萜烯合成酶或香叶基焦磷酸合成酶(gpps)和单萜合成酶代替香叶基香叶基焦磷酸合成酶(ggps)和二萜合成酶，构建产生各种类萜包括单萜和倍半萜烯的菌株。为了开发倍半萜烯生产菌株以测试cyp450用于新型含氧的萜烯，朱栾倍半萜合成酶被克隆并在mep途径过表达的大肠杆菌菌株中表达。高底物通量有助于识别cyp450的活性。以前，对含氧的紫杉二烯生产菌株的研究表明，当将cyp450途径转移到紫杉二烯生产菌株(300mg/l至～10mg/l)时，生产力显著降低。进一步地，应用多变量模块化代谢工程(mmme)来平衡朱栾倍半萜的高水平生产的途径。与获得100's的mg/l二类萜的先前结果相比，天然存在的朱栾倍半萜合成酶(诸如来自葡萄的朱栾倍半萜合成酶)，甚至在mmme优化后经常表现出次优化(～5mg/l)。涉及倍半萜烯生物合成的酶可能难以在大肠杆菌中表达，并且相对于涉及初级代谢(17)的那些，在动力学上也是有缺陷的。一种葡萄朱栾倍半萜合成酶(vvvs)的同源性模型使用软件包(schrodinger,inc.)构建，用5-非手性-马兜铃烯合成酶的晶体结构作为模板(pdb：5eat)。进一步地，为了识别萜烯合成酶的自然突变景观，产生了结合数百个相关萜烯合成酶序列的广泛的多序列比对。使用此信息，使用回归共识、计算机能量学(insilicoenergetics)和结构分析的组合设计突变。已显示回归共识突变是改善稳定性(19、20)和表达(21)的重要工具。使用基于bioluminate中的原子力场模型的能量计算来评估预测用于具有低溶剂可接近的表面积的位置的单个突变的折叠的δδg，其预期影响折叠和稳定性。通过应用mmme方法，在具有p15a复制起点和t7启动子的质粒上结合密码子优化形式的vvvs，识别平衡的上游和下游朱栾倍半萜生产菌株。然后将该菌株背景用于筛选设计的合成酶突变。使用上述蛋白工程工具，我们设计了超过200个独特的点突变(表3)，然后使用定点诱变在p15a-t7筛选质粒中构建该点突变。将突变的酶变体转化到筛选菌株中，将一式三份的菌落在选择性lb细胞培养基中培养过夜，然后接种到最小r培养基中并在22℃下培养4天。为了朱栾倍半萜的生产力，使用甲基叔丁基醚(mtbe)提取培养物，并通过组合气相色谱/质谱法分析培养物。大约五分之一的设计点突变在我们的筛选菌株中增加朱栾倍半萜生产力至少20％(图2)。然后将有益点突变策略性地组合以赋予越来越有利的表型。提供了重组的朱栾倍半萜合成酶序列如vv1m1(突变-r331k、i334e、n335s、v371i、a374l、t418v、s482t、s512p、k356n、q491k、e394d、a428v、y348f、t318s、l352i、i442l、a554p)、vv2m1(突变-r331k、i334e、n335s、v371i、a374l、t418v、s482t、s512p、k356n、q491k、e394d、a428v、v542t、g480a、m305l、k441r、a554p)、vv1m5(突变-r331k、i334e、n335s、v371i、a374l、t418v、s482t、s512p、k356n、q491k、e394d、a428v、y348f、t318s、l352i、i442l、a554p、h284m、c46k、f448t、q533e)和vv2m5(突变-r331k、i334e、n335s、v371i、a374l、t418v、s482t、s512p、k356n、q491k、e394d、a428v、v542t、g480a、m305l、k441r、a554p、h284m、c46k、f448t、q533e)(图3)。当这些酶中的任一种在具有dxs-idi-ispdf过表达且使用mmme平衡的我们的mep途径菌株中过表达时，所获得的朱栾倍半萜的滴度足以激发p450酶的掺入以测试其催化含氧的朱栾倍半萜形成的能力。掺入p450之前朱栾倍半萜的滴度为约30mg/l。实施例2：cyp450文库对朱栾倍半萜支架的功能活性使用朱栾倍半萜作为模型系统以验证基于cyp450的氧合化学用于生产萜烯化学品的能力。使用朱栾倍半萜生产大肠杆菌菌株作为宿主背景进行cypp450候选物筛选。为了构建用于功能性表达的cyp450，使用专有的质粒系统p5trc(源自psc101的质粒)构建含有通过柔性5-氨基酸连接子(gstgs，seqidno:117)融合至n端截短的甜菊细胞色素p450还原酶(srcpr)的候选p450的质粒。各种候选p450的序列显示在图4中。分析候选cyp450用于n端膜缔合区，n端膜结合区被截短，并向融合体中加入8个氨基酸的前导序列(malllavf，seqidno:112)(图5a和5b)。也在类似的遗传构建中制备来自拟南芥和红豆杉的cpr氧化还原配偶体(red/oxpartner)。由于天然srcpr是有效的，因此没有测定这些构建体的活性水平。各种cpr氧化还原配偶体的序列显示在图6中。在p5trc-cyp450-l-srcpr转化到朱栾倍半萜生产菌株后，菌株在抗生素选择性lb培养基中在30℃下培养过夜。然后将这些培养物用于接种无菌试管中的具有15g/l甘油和0.1mmiptg的2ml抗生素选择性r培养基培养物，随后在22℃下培养4天，然后用甲基叔丁基醚(mtbe)提取。从表4列出的那些中选择一组cyp450酶，并在这种大肠杆菌系统中分类为倍半萜烯和二萜氧合。在测试用于朱栾倍半萜氧合的各种cyp450酶中，发现来自甜菊(srko)(16)的贝壳杉烯氧化酶在朱栾倍半萜支架上具有独特的氧合化学。srko将c19位置的二萜(-)-贝壳杉烯自然地氧化为(-)-贝壳杉烯酸。srko酶在本研究中通过产生羟基化产物的不同的立体异构体(α和β诺特卡醇并进一步氧化成酮(诺卡酮))显示出独特的活性，并且产生不同的含氧的萜烯产物，除了α-诺特卡醇、β-诺特卡醇和诺卡酮之外，还包括羟基大根香叶-1(10)5-二烯、依兰烷-3,9(11)二烯-10-过氧化物。其他p450，包括先前已知的用于羟基化朱栾倍半萜的倍半萜烯cyp450，产生仅一种异构体(β诺特卡醇)和仅可检测量的酮(诺卡酮)。具体地，其它倍半萜烯cyp450酶产生β-诺特卡醇和羟基朱栾倍半萜作为主要产物，而另一种二萜cyp450酶(例如，紫杉属5-α羟化酶)产生诺特卡醇作为仅少量的(可检测的)产物(表4和图7)。表4：通过在大肠杆菌中选择p450酶从朱栾倍半萜形成的主要产物实施例3：srko的结构和突变研究一旦识别了srko的独特活性，进行实验以提高其进行朱栾倍半萜的不同氧化的能力。没有描述srko的晶体结构。针对rcsb蛋白数据库的srko的blast搜索显示了srko对于具有晶体结构的p450酶的序列同一性是低的(～20％)。鉴于p450的保守折叠结构，而不管其低的序列同一性，使用最先进技术的(state-of-the-art)蛋白建模工具建立在srko上。选择催化人雄激素生物合成的膜结合细胞色素p45017a1的晶体结构(参见devoren.m.,scotte.e.,nature,482,116-119,2012)作为模板用于模型开发。使用bioluminate蛋白建模软件，开发同源性模型(图8a)，使得关键残基和特征基序的定位(参见gotoho.,j.biolchem,267,83-90,1992)与模板良好比对。此外，还构建了包括修复的血红素铁复合物的srko的同源模型。然后使用autodockvina在srko活性位点中产生用于朱栾倍半萜的可能的结合模型的集合(图8b)(29)。此外，针对ncbi非冗余蛋白序列文库的srko的blast搜索没有返回序列同一性大于80％的直系同源物(srko本身除外)。顶部命中物列在表5中。表5：在制备同源模型中用srko的blast搜索一旦识别了srko的独特活性，进行实验以提高其进行朱栾倍半萜的不同氧化的能力。使用回归共识诱变策略，构建p450酶的多序列比对，包括来自使用4种种子贝壳杉烯氧化酶基因的uniref100数据库的blast搜索的序列(在聚集并消除具有大于90％同一性的序列之后)，来自使用p450bm3、p450cam和p450eryf作为种子基因的细菌蛋白质组的blast搜索的序列，以及最密切相关的srko同源物。基于同源性模型、多重序列比对和文献，设计并测试了各种点突变和双突变。在上述体内测试系统中评估这些细胞色素p450衍生物在总的含氧萜烯生产力(例如，通过gc/ms观察到的主峰的总数)中的改善。由模型指导的活性位点位置上的诱变揭示了具有显著改善的含氧产物的几种变体(下表6和下表7)。表6：与seqidno:38的srko相比的总含氧油的结合口袋突变及其倍数生产力表7：与seqidno:38的srko相比的总含氧油的非结合口袋点突变和生产力实施例4：诺卡酮的分离和评估通过gc/ms(agilent6800；柱：rtx-5，0.32mm×60m×1.0μm膜厚度；gc温度。程序：40℃持续5分钟，以4℃/min升至300℃并保持30分钟)分析由细胞色素p450酶srko(seqidno:38)的朱栾倍半萜的氧化得到的产物，得到表8a和8b中提供的数据。表8a.朱栾倍半萜的srko氧化表8b.朱栾倍半萜的srko氧化对由srko衍生物产生的产物进行类似的分析。证实了产物谱是可比的，并且可以基于srko的诱变以更高的水平产生诺卡酮、诺特卡醇的主要产物。然后可以使用合适的溶剂(例如庚烷)从水性反应介质中提取氧化的油产物，随后分馏。每个级分的化学组成可以通过gc/ms定量测量。可以混合级分以产生用于风味剂或其它应用的所需的诺特卡醇和/或诺卡酮成分。通过用表9中提供的分析直接与参考的诺卡酮调味产品(例如，从花臣香精(frutarom)获得的现有天然调味商业产品)比较，可以进行可接受的验证。表9.来自花臣香精的市售天然调味剂诺卡酮的分析实施例5：n端锚定工程化为了优化初始srko变体(在这些实施例中称为朱栾倍半萜氧化酶1或vo1)的膜相互作用，识别了锚定在具有胞质c端的内膜中的大肠杆菌蛋白。选择大肠杆菌yhcb的n端序列，其提供单次跨膜结构域。将来自yhcb的n端的20-24个氨基酸交换为原始膜锚定序列malllavf(seqidno:112)，并且srkon端截短的大小从28变为32。参见图9。vo1在p5质粒上的t7启动子的控制下表达。srcpr独立于染色体表达。如已经描述的，将菌株在96深孔板中在30℃下在r培养基加甘油和十二烷覆盖中培养48小时。如图10所示，与对照的平均值相比，n20yhcb_t29vo1在总含氧滴度中表现出1.2倍的生产力。n20yhcb_t29vo1表现出的总含氧滴度约为原始8rp锚的1.8倍(未显示)。实施例6：vo1的突变分析尽力进行vo1的突变分析以增加含氧滴度。使用菌株mb2509(mp6-mepmp1-scfppsfab46-vs2mp6-sccpr)作为背景，当用p5-t7-yhcb-vo1质粒转化时，产生约18％诺卡酮。为了诺卡酮的更高产量，评估菌株。在基于p45017a1(实施例3)的同源模型的指导下，在18位置进行vo活性位点的位点饱和诱变，构建5个成对位置文库。通过底物对接识别第一壳残基，并且基于用于改变结合口袋几何形状的相对接近性和位置选择非保守的第一壳残基。通过重叠延伸pcr和gibson组装构建成对位置文库。表12：成对位置文库(根据seqidno:37编号)为了朱栾倍半萜的总氧合作用，按照实施例4评估菌株。在30℃和22℃下评估菌株。成对位置文库的初步筛选揭示了一些变体失去活性。文库3包含在22℃而不是30℃具有改善的活性的变体。因此，在第一壳残基中同时引入两个或多个突变可能对活性有影响。表13：进行以下单一位置ssm(根据seqidno:37编号)几个变体改善含氧滴度高达1.7倍。在位置e323、i390和q500的突变显示出具有改善的氧合滴度的几个命中物，并且选择这些位置用于二次筛选。接下来，在vo1背景中筛选回归共识突变(19个突变体)。使用实施例3中所述的筛选方法，筛选以下突变：a2t、i389l、i389v、i389a、m94v、t488d、e491k、e52a、h46r、d191n、l150m、i495v、t468i、k344d、q268t、r351q、r76k、v400q和i444a(根据seqidno:37编号)。如图13a所示，超过50％的突变导致1.2至1.45倍的含氧滴度(显示为mg/l)，而产物谱中没有显著变化。用a2t、m94v、t488d、e52a、h46r、l150m、t468i、k344d、q268t、r351q、r76k、v400q和i444a，观察到改善，选择它们用于二次筛选。图13b显示了相对于倍数总含氧产物变化标绘的相同的筛选。选择来自活性位点ssm(l231m、i390l、i390m、t131k和t131q)的前导变体、n端锚定变体n20yhcb_t29vor1和回归共识诱变，并重新筛选。该二次筛选的结果显示在图14中。几个突变显示含氧滴度改善1.1-1.4倍。为了缩小用于重组的突变列表，在33℃筛选相同的突变以区分稳定的突变，稳定的突变可以使过程转换到更高的温度。如图15所示，6个突变(m94v、l150m、t468i、r76k、i390l和t131q)在33℃保持改善的生产力。除了前导n端锚定，选择这六个突变用于重组。实施例7：srko重组文库筛选通过在每个位点允许变体或野生型，将在二次筛选后选择的七个突变(实施例6)随机掺入到vo重组文库中。背景菌株是mb2509(egvg2mp6-cpr)+pbac-t7-bcd7-yhcb-vo。在30℃下初步筛选(使用实施例5中所述的相同方法)识别了几种变体，与vo1相比，在含氧产物滴度中具有高达1.35倍的改善。此外，选择变体显示生产转移到诺卡酮，表明了更高的p450活性(因为诺卡酮的生产需求两个氧合循环)。初级筛选的结果显示在图16a中(菌株对比以mg/l计的滴度)。图16b呈现了基于氧合能力(诺卡酮和诺特卡醇的总量)显示的相同筛选。然后在34℃和37℃下筛选重组变体以选择在更高温度下具有改善的活性和稳定性的前导序列。二级筛选的结果显示在图17中。虽然对照在37℃几乎完全无活性，但6个前导序列在较高温度下显示出有希望的活性，并被选择用于进一步筛选(c11(8)、b4(7)、c6(1)、c12(3)、b6(2)和c9(6))。基于该进一步筛选(图18)，基于氧合能力选择c6(1)作为最佳变体。六个前导序列包括以下组的突变。表14：来自重组文库的前导变体中的突变的组图23(a和b)显示了本文所述的几种工程化的朱栾倍半萜氧化酶(vo)变体的比对，并且突出了在筛选过程中评估的选择突变。在图23a中：8rp-t20srko(seqidno:106)是在n端具有20个氨基酸截短的srko序列，并且添加了8个氨基酸的膜锚定。8rp-t20vo0(seqidno:107)具有srkon端的20个氨基酸的截短、8个氨基酸的n端锚定的添加和位置499的单突变(根据野生型srko编号)。n22yhcb-t30vo1(seqidno:104)具有srkon端的30个氨基酸的截短，基于来自大肠杆菌yhcb的22个氨基酸的膜锚定，以及在位置46、231、284、383、400、488和499的8个点突变(相对于srko野生型)。n22yhcb-t30vo2(seqidno:105)具有srkon端的30个氨基酸截短，基于来自大肠杆菌yhcb的22个氨基酸的膜锚定，以及在位置76、94、131、231、284、383、390、468和499的9个点突变(相对于srko野生型)。在图24b中，显示针对野生型srko(seqidno:108)的vo0(seqidno:109)、vo1(seqidno:110)和vo2(seqidno:111)中的点突变(为了方便起见，所有用野生型srkon端显示)。实施例8：细胞色素p450还原酶筛选用vo1筛选一组细胞色素p450还原酶用于改善活性。使用菌株mb2459作为背景，用pbac-t7-bcd7-vo1(i382l)-t7bcdx-cprx进行该实施例。bcd代表bicistronicdesign，并描述于mutalik等人naturemethods2013(10)4:354中。较低的bcd数字是指较高的翻译率。cpr包括srcpr(seqidno:62)、srcpr3(seqidno:80)、aacpr(seqidno:68)、pgcpr(seqidno:82)、atcpr2(seqidno:72)、atcpr1(seqidno:70)、esrcpr1(seqidno:76)和eatr2(seqidno:74)。如实施例5中那样在30℃下测试菌株。如图20所示，通过rna测序研究获得的srcpr3在含氧滴度方面表现出1.3倍的改善。在34℃下重新测试cpr直系同源物。结果示于图20中。即使在较高温度下，srcpr3(seqidno:80)和aacpr(seqidno:68)都显示含氧滴度的1.3倍改善。含氧滴度与在30℃下获得的那些相当。实施例9：改变产物谱的醇脱氢酶评估了醇脱氢酶将诺特卡醇转化为诺卡酮的能力。评估了以下adh酶：表15：cpr酶使用mb2490作为背景菌株(mp6-mepfab46-scfpps-l-vs1mp6-vo1-o-srcpr+p5-t7-bcd14-adh)，如实施例5中那样评估菌株。简言之，mp6、fab46和t7是指用于连接的基因或操纵子的启动子。这里mep是过表达大肠杆菌dxs、idi和ispdf基因的操纵子。scfpps和vs1之间的l是指编码(gstgs)的短多肽连接子，而vo1和srcpr之间的-o-是指操纵子构建体，在该操纵子构建体中rbs序列插入在两个基因之间。加号表示质粒，加号后面描述为具有启动子、bcd(如上所述)和所讨论的adh的p5(5个拷贝)质粒。识别了四种直系同源物(vvdh、csaba2、bddh和zzsdr)，其将诺特卡醇转化成诺卡酮，导致诺卡酮滴度增加超过3倍。图21。参考文献1.qualleya，dudarevan.plantvolatiles.encycl.lifesci.2010；1-9.2.ajikumarp，tyok，carlsens.terpenoids：opportunitiesforbiosynthesisofnaturalproductdrugsusingengineeredmicroorganisms.mol.pharm.[internet].2008[cited2013may16]；5(2)：167-90.3.ajikumarpk，xiaow-h，tyokej，wangy，simeonf，leonarde，etal.isoprenoidpathwayoptimizationfortaxolprecursoroverproductioninescherichiacoli.science[internet].2010oct1[cited2013may22]；330(6000)：70-4.4.rod-k，paradiscem，ouelletm，fishcrkj，newmankl，ndungujm，ctal.productionoftheantimalarialdrugprecursorartemisinicacidinengineeredyeast.nature[internet].2006apr13[cited2013mar1]；440(7086)：940-3.5.sevrioukovaif，lih，zhangh，petersonja，poulostl.structureofacytochromcp450-rcdoxpartncrelcctron-transfcrcomplcx.proc.natl.acad.sci.u.s.a.[intcrnct].1999mar2；96(5)：1863-8.6.sevrioukovaif，poulostl.structuralbiologyofredoxpartnerinteractionsinp450cammonooxygcnasc：afreshlookatanoldsystcm.arch.biochcm.biophys.[internet].elsevierinc.；2011mar1[cited2013mar26]；507(1)：66-74.7.ekroosm，t.structuralbasisforligandpromiscuityincytochromep4503a4.proc.natl.acad.sci.u.s.a.[internet].2006sep12；103(37)：13682-7.8.takahashis，yeoy-s，zhaoy，o’maillepe，greenhagenbt，noeljp，etal.functionalcharacterizationofpremnaspirodieneoxygenase，acytochromep450catalyzingregio-andstereo-specifichydroxylationsofdiversesesqaiterpenesubstrates.j.biol.chem.[internet].2007oct26[cited2013mar10]；282(43)：31744-54.9.morroned，chenx，coatesrm，petersrj.characterizationofthekaureneoxidasccyp701a3，amultifunctionalcytochromcp450fromgibbcrcllinbiosynthesis.biochem.j.[internet].2010nov1[cited2013feb6]；431(3)：337-44.10.zhangz，sibbeseno.thesubstratespecificityofcytochromep450cam.bioorganicmed....[internet].1998[cited2013sep24]；6：1501-8.11.stjernschantze，vanvugt-lussenburgbma，bonifacioa，debeersba，vanderzwang，gooijerc，etal.structuralrationalizationofnoveldrugmetabolizingmutantsofcytochromep450bm3.proteins[internet].2008apr[cited2013may16]；71(1)：336-52.12.chenmmy，snowcd，vizearracl，mayosl，arnoldfh.comparisonofrandommutagcncsisandscmi-rationaldesigncdlibraricsforimprovedcytochromep450bm3-catalyzedhydroxylationofsmallalkanes.proteineng.des.sel.[internet].2012apr[cited2013mar11]；25(4)：171-8.13.harford-crosscf，carmichaelab，allanfk，englandpa，rouchda，wongll.proteinengineeringofcytochromep450(cam)(cyp101)fortheoxidationofpolycyclicaromatichydrocarbons.proteineng.[internet].2000fcb；13(2)：121-8.14.bellsg，chenx，sowdenrj，xuf，williamsjn，wongl，etal.molecularrecognitionin(+)-r-pineneoxidationbycytochromep450cam.j.am.chem.soc.2003；125：705-14.15.sowdenr，yasmins，reesn，bellsg，wongl-l.biotransformationofthesesquiterpene(+)-valencenebycytochromep450camandp450bm-3.org.biomol.chcm.[intcmct].2005[citcd2013may16]；3：57-64.16.brandleje，richmana，swansonak，chapmanbp.leafestsfromsteviarebaudiana：aresourceforgenediscoveryinditerpenesynthesis.plantmol.biol.[internet].2002nov[cited2013feb12]；50(4-5)：613-22.17.bar-evena，noore，saviry，liebermeisterw，davidid，tawfikds，etal.themoderatelyefficientenzyme：evolutionaryandphysicochemicaltrendsshapingenzymeparameters.biochemistry.2011；18.pleissj.proteindesigninmetabolicengineeringandsyntheticbiology.curr.opin.biotechnol.[internet].2011oct[cited2013mar5]；22(5)：611-7.19.lehmannm，pa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5240aspleuvalvalaspglyglyphethralavalthrasnvalmetser245250255metleugluglyhisgly260<210>89<211>789<212>dna<213>甜橙<400>89atgtcaaaaccgcgtctgcaaggcaaagtggctattattatgggtgctgcgtctggcatc60ggtgaagctacggctaaactgttcgctgaacatggcgcatttgtgattatcgctgatatt120caggacgaactgggcaaccaggtggttagctctatcggcccggaaaaagcgtcttatcgt180cactgcgatgtgcgtgatgaaaaacaggttgaagaaaccgtcgcgtatgcgattgaaaaa240tacggcagcctggatattatgtactccaatgcgggcgtggccggtccggttggcacgatt300ctggatctggacatggcccaattcgaccgtaccatcgcaacgaacctggctggtagtgtt360atggcagtcaaatatgcggcccgtgtcatggtggcgaataaaattcgcggtagcattatc420tgtaccacgagtaccgcctccacggtgggcggcagcggcccgcacgcctataccattagc480aaacacggtctgctgggcctggttcgttcagcagcttcggaactgggtaaacatggcatc540cgcgtgaactgcgttagcccgtttggtgttgcgaccccgttctctgccggtacgattaac600gatgtcgaaggctttgtctgtaaagtggcgaatctgaaaggcatcgtcctgaaagcgaag660catgtggccgaagcggccctgttcctggcaagcgatgaatctgcttatgtgagcggtcac720gacctggtggtggatggtggctttacggcagttacgaatgtcatgtcaatgctggaaggt780cacggctaa789<210>90<211>263<212>prt<213>甜橙<400>90metserasnproargmetgluglylysvalalaleuilethrglyala151015alaserglyileglyglualaalavalargleuphealagluhisgly202530alaphevalvalalaalaaspvalglnaspgluleuglyhisglnval354045alaalaservalglythraspglnvalcystyrhishiscysaspval505560argaspglulysglnvalglugluthrvalargtyrthrleuglulys65707580tyrglylysleuaspvalleupheserasnalaglyilemetglypro859095leuthrglyileleugluleuaspleuthrglypheglyasnthrmet100105110alathrasnvalcysglyvalalaalathrilelyshisalaalaarg115120125alametvalasplysasnileargglyserileilecysthrthrser130135140valalaserserleuglyglythralaprohisalatyrthrthrser145150155160lyshisalaleuvalglyleuvalargthralacyssergluleugly165170175alatyrglyileargvalasncysileserpropheglyvalalathr180185190proleusercysthralatyrasnleuargproaspgluvalgluala195200205asnsercysalaleualaasnleulysglyilevalleulysalalys210215220hisilealaglualaalaleupheleualaseraspgluseralatyr225230235240ileserglyhisasnleualavalaspglyglyphethrvalvalasn245250255hisserserserseralathr260<210>91<211>792<212>dna<213>甜橙<400>91atgtcaaacccgcgtatggaaggcaaagtcgcactgattacgggcgcagcatctggtatc60ggtgaagcagcagtccgtctgttcgctgaacatggtgcgtttgtcgtggcggcagatgtg120caagacgaactgggtcatcaggtggcggcatctgtgggtacggaccaggtgtgctaccat180cactgcgatgtgcgcgatgaaaaacaagtggaagaaaccgtgcgttataccctggaaaaa240tacggcaaactggatgtcctgttttcaaacgcgggcatcatgggtccgctgaccggcatt300ctggaactggatctgaccggcttcggtaacacgatggcaaccaatgtgtgcggtgttgcc360gcgaccattaaacacgcggcacgcgcaatggtggacaaaaacattcgcggtagcattatc420tgcaccaccagcgtggcttcatcgctgggtggcaccgcgccgcacgcatacaccacgagc480aaacacgcactggtgggcctggttcgtacggcatgttcggaactgggtgcgtatggcatt540cgtgtgaactgtatcagcccgtttggtgttgcaacgccgctgtcttgcacggcctataac600ctgcgcccggatgaagtggaagcaaactcatgcgcactggcgaacctgaaaggtattgtg660ctgaaagcgaaacacattgcggaagcagcgctgttcctggcgagcgatgaaagcgcgtat720attagcggtcataatctggcggtggatggtggtttcacggtggttaatcattcaagttcg780tcggcgacgtaa792<210>92<211>278<212>prt<213>甜橙<400>92metthrthralaglyserargaspserproleuvalalaglnargleu151015leuglylysvalalaleuvalthrglyglyalathrglyileglyglu202530serilevalargleuphehislyshisglyalalysvalcysvalval354045aspileasnaspaspleuglyglnhisleucysglnthrleuglypro505560thrthrargpheilehisglyaspvalalailegluaspaspvalser65707580argalavalaspphethrvalalaasnpheglythrleuaspilemet859095valasnasnalaglymetglyglyproprocysproaspileargglu100105110pheproileserthrpheglulysvalpheaspileasnthrlysgly115120125thrpheileglymetlyshisalaalaargvalmetileproserlys130135140lysglyserilevalserileserservalthrseralaileglygly145150155160alaglyprohisalatyrthralaserlyshisalavalleuglyleu165170175thrlysservalalaalagluleuglyglnhisglyileargvalasn180185190cysvalserprotyralaileleuthrasnleualaleualahisleu195200205hisgluaspgluargthraspaspalaargalaglypheargalaphe210215220ileglylysasnalaasnleuglnglyvalaspleuvalgluaspasp225230235240valalaasnalavalleupheleualaseraspaspalaargtyrile245250255serglyaspasnleuphevalaspglyglyphethrcysthrasnhis260265270serleuargvalphearg275<210>93<211>837<212>dna<213>甜橙<400>93atgacgacggctggttcgcgtgacagtccgctggtcgctcaacgcctgctgggcaaagtg60gccctggttacgggtggtgctaccggcattggtgaaagtatcgtgcgtctgtttcataaa120cacggcgcgaaagtttgcgtggttgatattaacgatgacctgggccagcatctgtgtcaa180accctgggtccgaccacccgtttcattcacggcgatgttgcaatcgaagatgatgtgagc240cgtgcggttgattttaccgtcgccaacttcggtacgctggacattatggtgaacaatgcc300ggtatgggcggtccgccgtgcccggatattcgtgaatttccgatctcgacctttgaaaaa360gtcttcgacattaacaccaaaggcacgttcatcggtatgaaacatgcggcccgcgtgatg420attccgagtaaaaaaggtagtattgtcagcattagcagcgtgaccagcgcgattggcggc480gcgggtccgcacgcctataccgcgagcaaacatgcggtgctgggcctgacgaaatctgtc540gcggcggaactgggccagcacggtattcgtgtcaactgtgtgtctccgtacgccatcctg600accaatctggcgctggcccatctgcacgaagatgaacgtacggatgacgcgcgtgcgggt660tttcgtgcattcattggtaaaaacgctaatctgcaaggtgttgatctggtcgaagatgac720gtggcgaatgccgttctgtttctggcatcagatgacgctcgctatatctcgggcgataac780ctgttcgtggatggcggcttcacctgtaccaatcactccctgcgtgtgttccgttaa837<210>94<211>280<212>prt<213>葡萄<400>94metalaalathrserileaspasnserproleuproserglnargleu151015leuglylysvalalaleuvalthrglyglyalathrglyileglyglu202530serilevalargleupheleulysglnglyalalysvalcysileval354045aspvalglnaspaspleuglyglnlysleucysaspthrleuglygly505560aspproasnvalserphephehiscysaspvalthrilegluaspasp65707580valcyshisalavalaspphethrvalthrlyspheglythrleuasp859095ilemetvalasnasnalaglymetalaglyproprocysseraspile100105110argasnvalgluvalsermetpheglulysvalpheaspvalasnval115120125lysglyvalpheleuglymetlyshisalaalaargilemetilepro130135140leulyslysglythrileileserleucysservalserseralaile145150155160alaglyvalglyprohisalatyrthrglyserlyscysalavalala165170175glyleuthrglnservalalaalaglumetglyglyhisglyilearg180185190valasncysileserprotyralailealathrglyleualaleuala195200205hisleuprogluaspgluargthrgluaspalametalaglyphearg210215220alaphevalglylysasnalaasnleuglnglyvalgluleuthrval225230235240aspaspvalalahisalaalavalpheleualaseraspglualaarg245250255tyrileserglyleuasnleumetleuaspglyglyphesercysthr260265270asnhisserleuargvalphearg275280<210>95<211>843<212>dna<213>葡萄<400>95atggccgcaacgagcattgataattctccgctgccgagtcaacgtctgctgggtaaagtc60gcactggtcacgggtggcgctacgggtattggcgaaagcatcgtgcgtctgtttctgaaa120cagggtgctaaagtgtgcattgtggacgtgcaagatgacctgggccagaaactgtgcgat180accctgggtggcgatccgaacgttagctttttccattgcgatgtgaccatcgaagatgat240gtgtgccatgcagttgattttaccgtcacgaaattcggcaccctggatattatggtgaac300aatgcgggtatggcaggtccgccgtgctcggacatccgcaacgtggaagtcagcatgttt360gaaaaagtgtttgatgtgaatgtgaaaggtgttttcctgggcatgaaacatgcagcccgc420attatgattccgctgaaaaaaggcaccattatcagcctgtgttcagtttccagcgctatc480gcgggcgttggtccgcacgcatatacgggtagcaaatgcgcagtggcgggtctgacgcaa540tcggtcgcagcagaaatgggtggtcatggcattcgcgtgaactgtatcagcccgtatgca600atcgcaacgggtctggcgctggcacatctgccggaagatgaacgcacggaagatgcaatg660gcgggtttccgtgcgtttgtgggtaaaaatgcgaatctgcaaggtgttgaactgaccgtg720gatgatgtggcgcacgcagcggtgtttctggcaagcgatgaagcacgttacatctctggt780ctgaatctgatgctggacggcggcttttcgtgtaccaaccactcgctgcgtgtctttcgc840taa843<210>96<211>279<212>prt<213>葡萄<400>96metserthralaserserglyaspvalserleuleuserglnargleu151015valglylysvalalaleuilethrglyglyalathrglyileglyglu202530serilealaargleuphetyrarghisglyalalysvalcysileval354045aspileglnaspasnproglyglnasnleucysarggluleuglythr505560aspaspalacysphephehiscysaspvalserilegluileaspval65707580ileargalavalaspphevalvalasnargpheglylysleuaspile859095metvalasnasnalaglyilealaaspproprocysproaspilearg100105110asnthraspleuserilepheglulysvalpheaspvalasnvallys115120125glythrpheglncysmetlyshisalaalaargvalmetvalprogln130135140lyslysglyserileileserleuthrservalalaservalilegly145150155160glyalaglyprohisalatyrthrglyserlyshisalavalleugly165170175leuthrlysservalalaalagluleuglyleuhisglyileargval180185190asncysvalserprotyralavalprothrglymetproleualahis195200205leuprogluserglulysthrgluaspalametmetglymetargala210215220phevalglyargasnalaasnleuglnglyilegluleuthrvalasp225230235240aspvalalaasnservalvalpheleualaseraspglualaargtyr245250255valserglyleuasnleumetleuaspglyglyphesercysvalasn260265270hisserleuargvalphearg275<210>97<211>840<212>dna<213>葡萄<400>97atgtcaacggcttcctcgggtgatgtgtcgctgctgtcgcaacgcctggtcggtaaagtc60gctctgattacgggtggtgcaacgggcattggtgaatcgattgcgcgtctgttttaccgt120catggtgcgaaagtgtgcatcgttgacattcaggataatccgggtcaaaacctgtgccgt180gaactgggcaccgacgatgcgtgcttctttcactgcgatgtgagcattgaaatcgatgtg240attcgtgctgttgactttgtggttaaccgctttggtaaactggacattatggttaataac300gcgggcatcgcagatccgccgtgcccggatattcgcaacaccgatctgagcatttttgaa360aaagtgttcgatgtgaacgtgaaaggcacctttcagtgtatgaaacacgcagcgcgcgtt420atggtgccgcagaaaaaaggtagcattatcagcctgacctcggtggcgagcgtgattggt480ggcgcgggtccgcacgcctatacgggtagcaaacacgcggttctgggtctgacgaaaagc540gttgcggcagaactgggtctgcatggtattcgcgtgaactgtgtgagtccgtatgcagtt600ccgacgggtatgccgctggcacatctgccggaatcggaaaaaaccgaagatgcgatgatg660ggtatgcgtgcatttgtgggtcgtaatgccaacctgcaaggtattgaactgaccgtggac720gatgtcgcaaatagcgtcgtgtttctggcgtcggatgaagcgcgttatgttagcggtctg780aacctgatgctggacggcggcttctcgtgtgtcaaccactcgctgcgtgtgtttcgctaa840<210>98<211>280<212>prt<213>甜橙<400>98metserasnserasnserthraspserserproalavalglnargleu151015valglyargvalalaleuilethrglyglyalathrglyileglyglu202530serthrvalargleuphehislyshisglyalalysvalcysileala354045aspvalglnaspasnleuglyglnglnvalcysglnserleuglygly505560gluproaspthrphephecyshiscysaspvalthrlysglugluasp65707580valcysseralavalaspleuthrvalglulyspheglythrleuasp859095ilemetvalasnasnalaglyileserglyalaprocysproaspile100105110argglualaaspleuserglupheglulysvalpheaspileasnval115120125lysglyvalphehisglymetlyshisalaalaargilemetilepro130135140glnthrlysglythrileileserilecysservalalaglyalaile145150155160glyglyleuglyprohisalatyrthrglyserlyshisalavalleu165170175glyleuasnlysasnvalalaalagluleuglylystyrglyilearg180185190valasncysvalserprotyralavalalathrglyleualaleuala195200205hisleuprogluglugluargthrgluaspalametvalglyphearg210215220asnphevalalaargasnalaasnmetglnglythrgluleuthrala225230235240asnaspvalalaasnalavalleupheleualaseraspglualaarg245250255tyrileserglythrasnleumetvalaspglyglyphethrserval260265270asnhisserleuargvalphearg275280<210>99<211>843<212>dna<213>甜橙<400>99atgtccaatagcaactctacggattcgtcgccggcagtccaacgcctggtcggtcgtgtc60gccctgattacgggtggtgcaacgggtattggcgaaagcacggtgcgcctgtttcataaa120catggcgcgaaagtgtgtattgccgacgttcaggataacctgggtcagcaagtgtgtcag180agtctgggtggcgaaccggatacctttttctgccattgtgatgtgacgaaagaagaagat240gtgtgtagcgcagttgatctgaccgtggaaaaatttggcaccctggacattatggtgaac300aatgcgggtattagcggcgca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151015glyalavalala20权利要求书(按照条约第19条的修改)1.一种制备倍半萜烯的含氧产物的方法，其包括使倍半萜烯与具有倍半萜烯氧化活性的甜菊贝壳杉烯氧化酶(srko)或其衍生物接触，以及回收所述含氧产物。2.如权利要求1所述的方法，其中所述srko衍生物包含相对于srko(seqidno:37、38或55)具有1-50个独立选自替换、缺失或插入的突变的氨基酸序列。3.如权利要求2所述的方法，其中所述srko衍生物包含相对于srko(seqidno:37、38或55)具有1-40个突变的氨基酸序列。4.如权利要求1-3中任一项所述的方法，其中所述srko衍生物包含与srko(seqidno:37、38或55)具有至少70％序列同一性的氨基酸序列，并且具有朱栾倍半萜氧化酶活性。5.如权利要求2-4中任一项所述的方法，其中相对于srko(seqidno:37、38或55)的一个或多个突变选自表2或表6。6.如权利要求5所述的方法，其中至少2个突变选自表2和/或表6。7.如权利要求2所述的方法，其中所述srko是缺失其n端跨膜区的至少一部分且添加来自大肠杆菌yhcb或其衍生物的内膜跨膜结构域的衍生物。8.如权利要求7所述的方法，其中所述srko是缺失其n端跨膜结构域的15-35个氨基酸且添加来自大肠杆菌yhcb或其衍生物的跨膜结构域的15-25个氨基酸的衍生物。9.如权利要求8所述的方法，其中来自yhcb的所述n端跨膜结构域包含seqidno:118的氨基酸序列或相对于seqidno:118具有1-5个氨基酸突变的氨基酸序列。10.如权利要求1-9中任一项所述的方法，其中所述srko是相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个或多个突变的衍生物。11.如权利要求10所述的方法，其中所述srko是相对于seqidno:37具有选自r76k、m94v、t131q、f231l、h284q、r383k、i390l、t468i和t499n的一个或多个突变的衍生物。12.如权利要求1所述的方法，其中所述srko是包含选自seqidno:55-61、104和105的氨基酸序列或相对于选自seqidno:55-61、104和105的序列具有1-20个突变的氨基酸序列的衍生物。13.如权利要求1-12中任一项所述的方法，其中所述倍半萜烯是朱栾倍半萜、大根香叶烯(a、b、c、d或e)、法尼烯、法尼醇、广藿香醇、杜松烯、雪松醇、蛇麻烯、长叶烯和/或佛手柑油烯、β-衣兰烯、β-檀香醇、β-檀香烯、α-檀香烯、α-檀香醇、β-香根酮、a-香根酮、客烯醇、红没药烯、β-丁香烯、长叶烯；α-甜橙醛；α-红没药醇、(-)-β-可巴烯、(-)-α-可巴烯、4(z),7(z)-癸二烯醛、雪松醇、雪松烯、雪松醇、愈创木醇、(-)-6,9-愈创木二烯、布藜醇、愈创木醇、喇叭烯、喇叭茶醇、香樟烯和α-佛手柑油烯。14.如权利要求1-13所述的方法，其中主要的倍半萜烯是朱栾倍半萜、大根香叶烯(a、b、c、d或e)、法尼烯、法尼醇、广藿香醇、杜松烯、雪松醇、蛇麻烯、长叶烯和/或佛手柑油烯、β-衣兰烯、β-檀香醇、β-檀香烯、α-檀香烯、α-檀香醇、β-香根酮、a-香根酮、客烯醇、红没药烯、β-丁香烯、长叶烯；α-甜橙醛；α-红没药醇、(-)-β-可巴烯、(-)-α-可巴烯、4(z),7(z)-癸二烯醛、雪松醇、雪松烯、雪松醇、愈创木醇、(-)-6,9-愈创木二烯、布藜醇、愈创木醇、喇叭烯、喇叭茶醇、香樟烯和α-佛手柑油烯。15.如权利要求14所述的方法，其中所述主要的倍半萜烯是朱栾倍半萜。16.如权利要求15所述的方法，其中主要的含氧产物是诺卡酮。17.如权利要求1-16中任一项所述的方法，其中所述接触发生在宿主细胞中，所述宿主细胞是细菌。18.如权利要求17所述的方法，其中所述宿主细胞是大肠杆菌、枯草芽孢杆菌或恶臭假单胞菌。19.如权利要求1-16中任一项所述的方法，其中所述接触发生在宿主细胞中，所述宿主细胞是酵母。20.如权利要求19所述的方法，其中所述宿主细胞是酵母属、毕赤酵母属或耶氏酵母属的种类，包括酿酒酵母、巴斯德毕赤酵母和解脂耶氏酵母。21.如权利要求17-20中任一项所述的方法，其中所述宿主细胞产生异戊基焦磷酸(ipp)。22.如权利要求21所述的方法，其中所述ipp经内源性或外源性mep或mva途径由代谢通量产生。23.如权利要求22所述的方法，其中所述倍半萜烯至少部分经mep途径由代谢通量产生，并且其中所述宿主细胞具有至少一个额外拷贝的dxs、ispd、ispf和/或idi基因。24.如权利要求17-23中任一项所述的方法，其中所述宿主细胞进一步表达法尼基焦磷酸合成酶。25.如权利要求17-24中任一项所述的方法，其中所述宿主细胞进一步表达异源倍半萜烯合成酶。26.如权利要求25所述的方法，其中所述倍半萜烯合成酶是朱栾倍半萜合成酶。27.如权利要求26所述的方法，其中所述朱栾倍半萜合成酶是甜橙或葡萄朱栾倍半萜合成酶或其衍生物。28.如权利要求21所述的方法，其中vvvs包含相对于vvvs(seqidno:1)具有1-40个独立选自替换、缺失或插入的突变的氨基酸序列。29.如权利要求27所述的方法，其中csvs包含相对于csvs(seqidno:12)具有1-40个独立选自替换、缺失或插入的突变的氨基酸序列。30.如权利要求28所述的方法，其中一个或多个突变选自表3。31.如权利要求1-30中任一项所述的方法，其中所述srko在共表达细胞色素p450还原酶的宿主细胞中表达。32.如权利要求31所述的方法，其中所述p450还原酶是来自甜菊属的cpr。33.如权利要求31所述的方法，其中所述p450还原酶包含选自seqidno:62、64、66、68、70、72、74、76、78、80和82的氨基酸序列或其衍生物。34.如权利要求1-33中任一项所述的方法，其中所述srko表达为具有细胞色素p450还原酶配偶体的融合体。35.如权利要求1-34中任一项所述的方法，其中所述宿主细胞进一步表达生产诺卡酮的醇脱氢酶。36.如权利要求1-35中任一项所述的方法，其中从水性反应介质中提取氧化油，然后进行分馏。37.如权利要求36所述的方法，其中使用有机溶剂从水性反应介质中提取所述氧化油。38.如权利要求36所述的方法，其中通过gc/ms定量测定级分中的倍半萜烯和类倍半萜烯组分，然后混合所述级分以生产所需的含诺卡酮的成分。39.如权利要求38所述的方法，其中定量测定诺卡酮组分。40.如权利要求36或37所述的方法，其中回收诺卡酮级分。41.一种制备含有含氧的倍半萜烯的产品的方法，其包括：将由权利要求1-40中任一项所述的方法制备的含氧的倍半萜烯掺入所述产品中。42.如权利要求41所述的方法，其中所述产品是风味产品、芳香产品、化妆品、清洁产品、洗涤剂或肥皂或害虫防治产品。43.如权利要求42所述的方法，其中所述产品是选自饮料、口香糖、糖果或人工风味剂的风味产品。44.如权利要求42所述的方法，其中所述产品是驱虫剂。45.一种srko衍生物，其包含相对于seqidno:37、38或55增加朱栾倍半萜氧化酶活性的至少一个突变。46.如权利要求45所述的srko衍生物，其中所述srko衍生物缺失其n端跨膜区的至少一部分，并且添加来自大肠杆菌yhcb或其衍生物的内膜跨膜结构域。47.如权利要求46所述的srko衍生物，其中所述srko衍生物缺失其n端跨膜结构域的15-35个氨基酸，并且添加来自大肠杆菌yhcb或其衍生物的跨膜结构域的15-25个氨基酸。48.如权利要求46所述的srko衍生物，其中所述n端跨膜结构域包含seqidno:118的氨基酸序列或相对于seqidno:118具有1-5个氨基酸突变的氨基酸序列。49.如权利要求45-48所述的srko衍生物，其中所述srko衍生物相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个或多个突变。50.如权利要求49所述的srko衍生物，其中所述srko衍生物相对于seqidno:37具有选自r76k、m94v、l107m、t131q、f231l、h284q、r383k、i390l、t468i和t499n的一个或多个突变。51.如权利要求50所述的srko衍生物，其中所述srko衍生物包含选自seqidno:55-61、104和105的氨基酸序列。52.如权利要求50所述的srko衍生物，其中所述srko衍生物包含相对于选自seqidno:55-61、104或105的氨基酸序列具有1-20个突变的氨基酸序列，附带条件是所述氨基酸序列相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个或多个突变，或附带条件是所述氨基酸序列相对于seqidno:37具有选自r76k、m94v、t131q、f231l、h284q、r383k、i390l、t468i和t499n的一个或多个突变。53.如权利要求45-52中任一项所述的srko衍生物，其中所述衍生物被分离或部分纯化，或在宿主细胞中异源表达。54.一种生产含氧的倍半萜烯的宿主细胞，其中所述宿主细胞产生异戊基焦磷酸(ipp)；并且所述宿主细胞表达法尼基焦磷酸合成酶、倍半萜烯合成酶和具有朱栾倍半萜氧化酶活性的srko或其衍生物。55.如权利要求54所述的宿主细胞，其中所述srko衍生物包含相对于seqidno:37、38或55增加朱栾倍半萜氧化酶活性的至少一个突变56.如权利要求54或55所述的宿主细胞，其中所述宿主细胞表达mva或mep途径。57.如权利要求56所述的宿主细胞，其中所述宿主细胞是细菌或酵母。58.如权利要求57所述的宿主细胞，其中所述宿主细胞是大肠杆菌、枯草芽孢杆菌或恶臭假单胞菌。59.如权利要求57所述的宿主细胞，其中所述宿主细胞是酵母属、毕赤酵母属或耶氏酵母属的种类，包括酿酒酵母、巴斯德毕赤酵母和解脂耶氏酵母。60.如权利要求54-59中任一项所述的宿主细胞，其中所述srko衍生物相对于srko(seqidno:37、38或55)具有1-50个独立选自替换、缺失或插入的突变。61.如权利要求60所述的宿主细胞，其中所述srko衍生物相对于srko(seqidno:37、38或55)具有1-40个突变。62.如权利要求60或61所述的宿主细胞，其中所述srko衍生物包含与srko(seqidno:37、38或55)具有至少70％序列同一性的氨基酸序列，并且具有朱栾倍半萜氧化酶活性。63.如权利要求54-62中任一项所述的宿主细胞，其中相对于srko(seqidno:37或38)的一个或多个突变选自表2或表6。64.如权利要求63所述的宿主细胞，其中至少2个突变选自表2和/或表6。65.如权利要求54所述的宿主细胞，其中所述srko衍生物缺失其n端跨膜区的至少一部分，并且添加来自大肠杆菌yhcb或其衍生物的内膜跨膜结构域。66.如权利要求65所述的宿主细胞，其中所述srko衍生物缺失其n端跨膜结构域的15-35个氨基酸，并且添加来自大肠杆菌yhcb或其衍生物的跨膜结构域的15-25个氨基酸。67.如权利要求66所述的宿主细胞，其中所述n端跨膜结构域包含seqidno:118的氨基酸序列或相对于seqidno:118具有1-5个氨基酸突变的氨基酸序列。68.如权利要求54-67中任一项所述的宿主细胞，其中所述srko衍生物相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个或多个突变。69.如权利要求68所述的宿主细胞，其中所述srko衍生物相对于seqidno:37具有选自r76k、m94v、l107m、t131q、f231l、h284q、r383k、i390l、t468i和t499n的一个或多个突变。70.如权利要求68或69所述的宿主细胞，其中所述srko衍生物包含选自seqidno:55-61、104和105的氨基酸序列；或相对于选自seqidno:55-61、104和105的序列具有1-20个突变的氨基酸序列，附带条件是所述氨基酸序列相对于seqidno:37在选自46、76、94、131、231、284、383、390、400、444、468、488和499的位置具有一个或多个突变，或附带条件是所述氨基酸序列相对于seqidno:37具有选自r76k、m94v、t131q、f231l、h284q、r383k、i390l、t468i和t499n的一个或多个突变。71.如权利要求54-70中任一项所述的宿主细胞，其中所述宿主细胞生产诺卡酮。72.如权利要求71所述的宿主细胞，其中所述宿主细胞是具有至少一个额外拷贝的dxs、ispd、ispf和/或idi基因的大肠杆菌。73.如权利要求54-72中任一项所述的宿主细胞，其中所述倍半萜烯合成酶是朱栾倍半萜合成酶。74.如权利要求73所述的宿主细胞，其中所述朱栾倍半萜合成酶是在大肠杆菌中具有增加的表达和/或活性的甜橙或葡萄朱栾倍半萜合成酶或其衍生物。75.如权利要求74所述的宿主细胞，其中vvvs衍生物相对于vvvs(seqidno:1)具有1-40个独立选自替换、缺失或插入的突变。76.如权利要求74所述的宿主细胞，其中csvs相对于csvs(seqidno:12)具有1-40个独立选自替换、缺失或插入的突变。77.如权利要求75所述的宿主细胞，其中一个或多个突变选自表3。78.如权利要求54-77中任一项所述的宿主细胞，其中所述srko或其衍生物在共表达细胞色素p450还原酶的宿主细胞中表达。79.如权利要求78所述的宿主细胞，其中所述srko表达为具有细胞色素p450还原酶配偶体的融合体。80.如权利要求54-79中任一项所述的宿主细胞，其中所述p450还原酶是来自甜菊属的cpr。81.如权利要求54-79中任一项所述的宿主细胞，其中所述p450还原酶包含选自seqidno:62、64、66、68、70、72、74、76、78、80和82的氨基酸序列或其衍生物。82.如权利要求54-79中任一项所述的宿主细胞，其中所述宿主细胞进一步表达将诺特卡醇转化为诺卡酮的醇脱氢酶。83.一种含氧的倍半萜烯产物，其由权利要求1-40中任一项所述的方法获得。84.一种风味产品或芳香产品，其包含如权利要求83中所限定的含氧的倍半萜烯产物。85.一种驱虫剂产品，其包含如权利要求83中所限定的含氧的倍半萜烯产物。86.一种朱栾倍半萜合成酶，其包含在大肠杆菌中具有增加的活性的选自seqidno:3(vv1mi)、seqidno:5(vv2mi)、seqidno:7(vv1m5)、seqidno:9(vv2m5)和seqidno:11(vs2)的氨基酸序列或其衍生物。87.一种重组核酸分子，其包含核苷酸序列，所述核苷酸序列编码具有增加朱栾倍半萜氧化酶活性的至少一个突变的srko衍生物；前导序列，所述前导序列支持在大肠杆菌中的表达和活性；连接子序列；和srcpr或其衍生物，所述srcpr或其衍生物足以再生所述srko衍生物。88.一种重组核酸分子，其包含编码权利要求45-52中任一项所述的srko衍生物的核苷酸序列。89.一种分离的核苷酸序列、重组载体或宿主细胞，其包含编码根据权利要求88所述的修饰的srko多肽的核苷酸序列。90.一种权利要求88所述的分离的核苷酸序列，其中所述核苷酸序列在宿主细胞中表达，并且其中所述宿主细胞是大肠杆菌细胞。91.一种制备根据权利要求45-52所述的修饰的srko多肽的方法，其中所述方法包括如下步骤：(i)在允许多肽表达的条件下，培养表达修饰多肽的宿主细胞；和(ii)任选地回收所述多肽。92.一种生产含氧的倍半萜烯的方法，其包括如下步骤：(i)提供根据权利要求45或52所述的修饰的srko多肽(ii)在细胞色素p450还原酶的存在下，使倍半萜烯与修饰的srko多肽接触，和(iii)回收生产的含氧的倍半萜烯。93.根据权利要求92所述的方法，其中回收所述含氧的倍半萜烯作为油。94.根据权利要求91-93所述的方法，其中所述倍半萜烯是朱栾倍半萜。当前第1页12当前第1页12