(+)-copalyl diphosphate | 19380-47-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-copalyl diphosphate
• 英文别名: (5S,9S,10S)-copalyl diphosphate；(5S,9S,10S)-CPP；Copalyl diphosphate；[(E)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enyl] phosphono hydrogen phosphate
• CAS: 19380-47-3
• 化学式: C₂₀H₃₆O₇P₂
• 分子量: 450.449
• InChiKey: JCAIWDXKLCEQEO-ATPOGHATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-copalyl diphosphate 在 calf intestinal phosphatase 作用下， 反应 4.0h， 生成 2-戊烯-1-醇,5-[(1S,4aS,8aS)-十氢-5,5,8a-三甲基-2-亚甲基-1-萘基]-3-甲基-,(2E)-
  参考文献：
  名称：

  A Functional Genomics Approach to Tanshinone Biosynthesis Provides Stereochemical Insights

  摘要：

  Tanshinones are abietane-type norditerpenoid quinone natural products that are the bioactive components of the Chinese medicinal herb Salvia miltiorrhiza Bunge. The initial results from a functional genomics-based investigation of tanshinone biosynthesis, specifically the functional identification of the relevant diterpene synthases from S. miltiorrhiza, are reported, The cyclohexa-1,4-diene arrangement of the distal ring poises the resulting miltiradiene for the ensuing aromatization and hydroxylation to ferruginol suggested for tanshinone biosynthesis.

  DOI：

  10.1021/ol902051v
• 作为产物：
  描述：

  牛儿基牛儿基焦磷酸三铵盐 在 Salvia miltiorrhiza Bunge recombinant labdadienyl/copalyl diphosphate synthase 、 potassium chloride 、 sodium phosphate 、 magnesium chloride 、 1,4-二巯基-2,3-丁二醇 、 4-羟乙基哌嗪乙磺酸 作用下， 以 甘油 为溶剂， 反应 2.0h， 生成 (+)-copalyl diphosphate
  参考文献：
  名称：

  A Functional Genomics Approach to Tanshinone Biosynthesis Provides Stereochemical Insights

  摘要：

  Tanshinones are abietane-type norditerpenoid quinone natural products that are the bioactive components of the Chinese medicinal herb Salvia miltiorrhiza Bunge. The initial results from a functional genomics-based investigation of tanshinone biosynthesis, specifically the functional identification of the relevant diterpene synthases from S. miltiorrhiza, are reported, The cyclohexa-1,4-diene arrangement of the distal ring poises the resulting miltiradiene for the ensuing aromatization and hydroxylation to ferruginol suggested for tanshinone biosynthesis.

  DOI：

  10.1021/ol902051v

文献信息

• Terpene Synthases and Methods of Using the Same
  申请人：University of Tennessee Research Foundation

  公开号：US20140030784A1

  公开（公告）日：2014-01-30

  Disclosed are isolated nucleic acid molecules from Selaginella moellendorffii that encode a terpene synthase protein at least 80% identical to a protein encoded by the nucleic acid sequence according to any of SEQ ID NOs: 1-47 or a degenerate variant thereof or a functional fragment thereof. Isolated terpene synthase proteins from S. moellendorffii are also disclosed. Host cells transformed with the S. moellendorffii terpene synthase nucleic acids are also disclosed, for example cells of a single cell organism, such as bacteria and yeast, or multicellular organism, such as a plant. The host cells can be prokaryotic cells or eukaryotic cells. Transgenic plants, or any part thereof, stably transformed with S. moellendorffii terpene synthase nucleic acids are also disclosed In some examples the transgenic plant is a dicotyledon or a monocotyledon. A method is disclosed for producing a transgenic plant, as is a method for producing terpenes.

  本文揭示了来自墨西哥卷柏（Selaginella moellendorffii）的分离核酸分子，其编码至少与序列编号为SEQ ID NOs: 1-47或其变异体或其功能片段编码的萜类合成酶蛋白80％相同。此外，还揭示了来自S. moellendorffii的分离萜类合成酶蛋白。此外，还揭示了转化了S. moellendorffii萜类合成酶核酸的宿主细胞，例如单细胞生物（如细菌和酵母）或多细胞生物（如植物）。宿主细胞可以是原核细胞或真核细胞。此外，还揭示了转基因植物或其任何部分，其稳定转化了S. moellendorffii萜类合成酶核酸。在某些实例中，转基因植物是双子叶植物或单子叶植物。本文还揭示了一种生产转基因植物的方法，以及一种生产萜类化合物的方法。
• Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals
  作者：Dana Morrone、Matthew L. Hillwig、Matthew E. Mead、Luke Lowry、D. Bruce Fulton、Reuben J. Peters

  DOI：10.1042/bj20101429

  日期：2011.5.1

  The evolution of natural product biosynthetic pathways can be envisioned to occur via a number of mechanisms. In the present study we provide evidence that latent plasticity plays a role in such metabolic evolution. In particular, rice (Oryza sativa) produces both ent- and syn-CPP (copalyl diphosphate), which are substrates for downstream diterpene synthases. In the present paper we report that several members of this enzymatic family exhibit dual reactivity with some pairing of ent-, syn- or normal CPP stereochemistry. Evident plasticity was observed, as a previously reported ent-sandaracopimaradiene synthase also converts syn-CPP into syn-labda-8(17),12E,14-triene, which can be found in planta. Notably, normal CPP is not naturally found in rice. Thus the presence of diterpene synthases that react with this non-native metabolite reveals latent enzymatic/metabolic plasticity, providing biochemical capacity for utilization of such a novel substrate (i.e. normal CPP) which may arise during evolution, the implications of which are discussed.

  天然产物生物合成途径的进化可通过多种机制实现。本研究提供的证据表明，潜在的可塑性在这种代谢进化中发挥了作用。特别是，水稻（Oryza sativa）同时产生ent-和syn-CPP（共聚二磷酸），它们是下游二萜合成酶的底物。在本文中，我们报告了该酶家族中的几个成员表现出了双重反应性，它们在ent-、syn-或正常 CPP 立体化学上有一些配对。我们观察到了明显的可塑性，因为之前报道的一种ent-sandaracopimaradiene合成酶也能将syn-CPP转化为syn-labda-8(17),12E,14-triene，这在植物体内也能发现。值得注意的是，水稻中并不天然存在正常的 CPP。因此，与这种非本地代谢物发生反应的二萜合成酶的存在揭示了潜在的酶/代谢可塑性，为利用这种可能在进化过程中产生的新型底物（即正常 CPP）提供了生化能力，其意义将在本文中讨论。
• Method for biocatalytic production of terpene compounds
  申请人：FIRMENICH SA

  公开号：US11214775B2

  公开（公告）日：2022-01-04

  Provided herein are biocatalytic methods of producing terpene compounds by applying a novel type of phosphatase enzyme. The method allows the fully biochemical synthesis of terpene compounds, like for example copalol and labdendiol, and derivatives thereof, which serve as valuable intermediates for the production of perfumery ingredients, such as, for example, ambrox. Also provided are novel fully biochemical multistep processes for the production of such compounds as well as novel phosphatase enzymes and mutants and variants derived therefrom.

  本文提供了通过应用一种新型磷酸酶生产萜烯化合物的生物催化方法。这种方法可以完全生化合成萜烯化合物，例如 copalol 和 labdendiol 及其衍生物，它们是生产香水成分（例如 ambrox）的重要中间体。此外，还提供了生产此类化合物的新型全生化多步骤工艺，以及新型磷酸酶和由其衍生的突变体和变体。
• METHOD FOR BIOCATALYTIC PRODUCTION OF TERPENE COMPOUNDS
  申请人：FIRMENICH SA

  公开号：US20210222138A1

  公开（公告）日：2021-07-22

  Provided herein are biocatalytic methods of producing terpene compounds by applying a novel type of phosphatase enzyme. The method allows the fully biochemical synthesis of terpene compounds, like for example copalol and labdendiol, and derivatives thereof, which serve as valuable intermediates for the production of perfumery ingredients, such as, for example, ambrox. Also provided are novel fully biochemical multistep processes for the production of such compounds as well as novel phosphatase enzymes and mutants and variants derived therefrom.
• [EN] BIOCATALYTIC METHOD FOR THE CONTROLLED DEGRADATION OF TERPENE COMPOUNDS<br/>[FR] PROCÉDÉ BIOCATALYTIQUE POUR LA DÉGRADATION MAÎTRISÉE DE COMPOSÉS TERPÉNIQUES
  申请人：FIRMENICH & CIE

  公开号：WO2021005097A9

  公开（公告）日：2022-02-24

  [EN] Provided herein are biocatalytic methods of producing terpene degradation products useful as starting material for the production of perfumery ingredients, such as, for example, ambrox. In particular novel terpene degrading polypeptides (enal-cleaving polypeptides) and novel peptides converting terpenes compounds to oxygenated derivatives (oxygenases) and mutants and variants derived therefrom are provided which may be applied in novel types of fully enzymatic multistep degradation pathways allowing the controlled, stepwise conversion and degradation of linear or cyclic terpene substrates. Said novel biosynthetic strategies allow the fully biochemical synthesis of valuable terpene-derived compounds, like for example manooloxy or gamma ambrol. The invention also provides recombinant host organisms carrying the required set of genetic information for the functional expression of the set of enzymes necessary for catalyzing the combination of enzymatic conversion and degradation steps.
  [FR] L'invention concerne des procédés biocatalytiques de production de produits de dégradation de terpènes utiles en tant que matière de départ pour la production d'ingrédients de parfumerie, tels que, par exemple, l'ambrox. En particulier, l'invention concerne de nouveaux polypeptides de dégradation de terpènes (polypeptides de clivage d'énal) et de nouveaux peptides qui convertissent des composés terpènes en dérivés oxygénés (oxygénases) et des mutants et des variants dérivés de ces derniers, qui peuvent être appliqués dans de nouveaux types de voies de dégradation multi-étapes entièrement enzymatiques permettant la conversion progressive, maîtrisée et la dégradation de substrats terpéniques linéaires ou cycliques. Lesdites nouvelles stratégies de biosynthèse permettent la synthèse entièrement biochimique de composés dérivés de terpènes valorisables, comme par exemple le manooloxy ou le gamma ambrol. L'invention concerne également des organismes hôtes recombinants véhiculant l'ensemble requis d'informations génétiques pour l'expression fonctionnelle de l'ensemble d'enzymes nécessaires pour catalyser la combinaison d'étapes de conversion et de dégradation enzymatiques.