cis-muurola-4(14),5-diene | 84236-09-9

• 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: cis-muurola-4(14),5-diene
• 英文别名: (1R,4R,4aS)-4-methyl-7-methylidene-1-propan-2-yl-2,3,4,4a,5,6-hexahydro-1H-naphthalene
• CAS: 84236-09-9
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: RNDFUOKDULDZPR-MCIONIFRSA-N

物化性质

• 沸点：
  281.3±7.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)
• 保留指数：
  1491;1467;1468

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：

  cis-14-nor-muurol-5-ene-4-one 、 亚甲基三苯基膦烷 在 potassium tert-butylate 作用下， 反应 2.0h， 生成 cis-muurola-4(14),5-diene
  参考文献：
  名称：

  Rangaishenvi, M. V.; Hiremath, S. V.; Kulkarni,Sheshgiri N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 7, p. 678 - 679

  摘要：

  DOI：

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.
• Rangaishenvi, M. V.; Hiremath, S. V.; Kulkarni,Sheshgiri N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. <B> 21, # 7, p. 678 - 679
  作者：Rangaishenvi, M. V.、Hiremath, S. V.、Kulkarni,Sheshgiri N.

  DOI：——

  日期：——