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.