Α-杜松烯 | 24406-05-1

• 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
• 中文名称: Α-杜松烯
• 英文名称: α‐cadinene
• 英文别名: α–cadinene；(-)-α-cadinene；α-cadinene；β-Cadinene；γ-cadinene；δ-cadinene；alpha-Cadinene, (+)-；(1S,4aR,8aR)-4,7-dimethyl-1-propan-2-yl-1,2,4a,5,6,8a-hexahydronaphthalene
• CAS: 24406-05-1
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: QMAYBMKBYCGXDH-KKUMJFAQSA-N

物化性质

• 沸点：
  271.5±30.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)
• LogP：
  6.557 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  farnesyl pyrophosphate 生成 Α-杜松烯 、 pyrophosphoric acid
  参考文献：
  名称：

  黑胡椒（Piper nigrum）未成熟果实中三种萜烯合成酶的分子克隆和功能表征。

  摘要：

  为了鉴定负责倍半萜生物合成的萜烯合酶（TPS），该倍半萜有助于黑胡椒（Piper nigrum）的风味，对未成熟的胡椒进行了Illumina转录组测序。使用amorpha-4,11-diene合酶作为查询的BLAST分析确定了19个倍半萜烯合酶（sesqui-TPSs），其中克隆了三个全长cDNA（PnTPS1至3）。这些sesqui-TPS cDNA在大肠杆菌中表达以产生用于体外测定的重组酶，还在工程酵母菌株中表达以评估其体内催化活性。。PnTPS1以β-石竹烯为主要产物，以mul草烯为次要化合物，因此被称为石竹烯合酶（PnCPS）。同样，PnTPS2和PnTPS3分别被称为卡丁酚/卡丹烯合酶（PnCO / CDS）和germ啶D合成酶（PnGDS）。酵母中PnGDS的表达产生了-丁二烯D的重排产物β-cadinene和α-copaene。它们的k cat / K m值（20–37.7 s

  DOI：

  10.1016/j.abb.2017.12.011

文献信息

• Cloning and functional characterisation of a cis-muuroladiene synthase from black peppermint (Mentha×piperita) and direct evidence for a chemotype unable to synthesise farnesene
  作者：Ian M. Prosser、Racheal J. Adams、Michael H. Beale、Nathan D. Hawkins、Andrew L. Phillips、John A. Pickett、Linda M. Field

  DOI：10.1016/j.phytochem.2005.06.012

  日期：2006.8

  Using oligonucleotide primers designed to the known gene sequence of an (E)-beta-farnesene (E beta F) synthase, two cDNA sequences (MxpSS1 and MxpSS2) were cloned from a black peppermint (Mentha x piperita) plant. MxpSS1 encoded a protein with 96% overall amino acid sequence identity with the E beta F synthase. Recombinant MxpSS1 produced in Escherichia coli, after removal of an N-terminal thioredoxin fusion, had a K-m for FPP of 1.91 +/- 0.1 mu M and k(cat), of 0-18 s(-1) and converted farnesyl diphosphate (FPP) into four products, the major two being cis-muurola-3,5-diene (45%) and cis-muurola-4(14),5-diene (43%). This is the first cis-muuroladiene synthase, to be characterised. MxpSS2 encoded a protein with only two amino acids differing from E beta F synthase. Recombinant MxpSS2 protein showed no activity towards FPP. One of the two mutations, at position 531 (leucine in MxpSS2 and serine in E beta F synthase) was shown, by structural modelling to occur in the J-K loop, an element of the structure of sesquiterpene synthases known to be important in the reaction mechanism. Reintroduction of the serine at position 531 into MxpSS2 by site-directed mutagenesis restored E beta F synthase activity (K. for FPP 0.98 +/- 0.12 pM, k(cat) 0-1 s(-1)), demonstrating the crucial role of this residue in the enzyme activity. Analysis, by GC-MS, of the sesquiterpene profile of the plant used for the cloning, revealed that E beta F was not present, confirming that this particular mint chemotype had lost E beta F synthase activity due to the observed mutations. (c) 2005 Elsevier Ltd. All rights reserved.
• Molecular cloning and functional characterization of three terpene synthases from unripe fruit of black pepper (Piper nigrum)
  作者：Zhehao Jin、Moonhyuk Kwon、Ah-Reum Lee、Dae-Kyun Ro、Juraithip Wungsintaweekul、Soo-Un Kim

  DOI：10.1016/j.abb.2017.12.011

  日期：2018.1

  identify terpene synthases (TPS) responsible for the biosynthesis of the sesquiterpenes that contribute to the characteristic flavors of black pepper (Piper nigrum), unripe peppercorn was subjected to the Illumina transcriptome sequencing. The BLAST analysis using amorpha-4,11-diene synthase as a query identified 19 sesquiterpene synthases (sesqui-TPSs), of which three full-length cDNAs (PnTPS1 through

  为了鉴定负责倍半萜生物合成的萜烯合酶（TPS），该倍半萜有助于黑胡椒（Piper nigrum）的风味，对未成熟的胡椒进行了Illumina转录组测序。使用amorpha-4,11-diene合酶作为查询的BLAST分析确定了19个倍半萜烯合酶（sesqui-TPSs），其中克隆了三个全长cDNA（PnTPS1至3）。这些sesqui-TPS cDNA在大肠杆菌中表达以产生用于体外测定的重组酶，还在工程酵母菌株中表达以评估其体内催化活性。。PnTPS1以β-石竹烯为主要产物，以mul草烯为次要化合物，因此被称为石竹烯合酶（PnCPS）。同样，PnTPS2和PnTPS3分别被称为卡丁酚/卡丹烯合酶（PnCO / CDS）和germ啶D合成酶（PnGDS）。酵母中PnGDS的表达产生了-丁二烯D的重排产物β-cadinene和α-copaene。它们的k cat / K m值（20–37.7 s