3β-Hydroxy-protosta-17(20)<16,21:cis>,24-dien | 22879-37-4

• 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: 3β-Hydroxy-protosta-17(20)<16,21:cis>,24-dien
• 英文别名: seqcis-3β-Hydroxy-4-methyl-fusidadien-(17(20),24); seqcis-3β-Hydroxyprotostadien-(17(20),24)；(17Z)-protosta-17(20),24-dien-3β-ol；protosta-17(20)Z,24-dien-3β-ol；(17Z)-protosta-17(20),24-dien-3beta-ol；(3S,5R,8S,9S,10R,13S,14S,17Z)-4,4,8,10,14-pentamethyl-17-(6-methylhept-5-en-2-ylidene)-1,2,3,5,6,7,9,11,12,13,15,16-dodecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 22879-37-4
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: CKYVHRSYUPJCLG-PTZNGALWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-Hydroxy-protosta-17(20)<16,21:cis>,24-dien 在 盐酸 作用下， 以 氯仿 、 水 为溶剂， 反应 24.0h， 生成 (20R)-protosta-13(17),24-dien-3β-ol
  参考文献：
  名称：

  Mitsuguchi, Hisashi; Seshime, Yasuyo; Fujii, Isao, Journal of the American Chemical Society, 2009, vol. 131, p. 6402 - 6411

  摘要：

  DOI：
• 作为产物：
  描述：

  squalene 2,3(S)-oxide 生成 3β-Hydroxy-protosta-17(20)<16,21:cis>,24-dien
  参考文献：
  名称：

  Protostadienol Biosynthesis and Metabolism in the Pathogenic Fungus Aspergillus fumigatus

  摘要：

  Details of the fungal biosynthetic pathway to helvolic acid and other fusidane antibiotics remain obscure. During product characterization of oxidosqualene cyclases; in Aspergillus fumigatus, we found the long-sought cyclase that makes (17Z)-protosta-17(20),24-dien-3 beta-ol, the precursor of helvolic acid. We then identified a gene cluster encoding the pathway to helvolic acid, which is controlled by a transcription regulator (LaeA) associated with fungal virulence. Evidence regarding the evolutionary origin and taxonomic distribution of fusidane biosynthesis is also presented.

  DOI：

  10.1021/ol802696a

文献信息

• Protostadienol synthase from Aspergillus fumigatus: Functional conversion into lanosterol synthase
  作者：Miki Kimura、Tetsuo Kushiro、Masaaki Shibuya、Yutaka Ebizuka、Ikuro Abe

  DOI：10.1016/j.bbrc.2009.11.160

  日期：2010.1

  Oxidosqualene:protostadienol cyclase (OSPC) from the fungus Aspergillus fumigatus, catalyzes the cyclization of (3S)-2,3-oxidosqualene into protosta-17(20)Z,24-dien-3 beta-ol which is the precursor of the steroidal antibiotic helvolic acid. To shed light on the structure-function relationship between OSPC and oxidosqualene-lanosterol cyclase (OSLC). we constructed an OSPC Mutant in which the C-terminal residues (702)APPGGMR(708) were replaced with (702)NKSCAIS(708), as in human OSLC As a result, the mutant no longer produced the protostadienol, but instead efficiently produced a 11 mixture of lanosterol and parkeol This is the first report of the functional conversion of OSPC into OSLC, which resulted in a 14-fold decrease in the V-max/K-M value, whereas the binding affinity for the substrate did not change significantly Homology modeling suggested that stabilization of the C-20 protosteryl cation by the active-site Phe701 through cation-pi interactions is Important for the product outcome between protostadienol and lanosterol. (C) 2009 Elsevier Inc. All rights reserved
• Protostadienol Biosynthesis and Metabolism in the Pathogenic Fungus <i>Aspergillus fumigatus</i>
  作者：Silvia Lodeiro、Quanbo Xiong、William K. Wilson、Yulia Ivanova、McKenzie L. Smith、Gregory S. May、Seiichi P. T. Matsuda

  DOI：10.1021/ol802696a

  日期：2009.3.19

  Details of the fungal biosynthetic pathway to helvolic acid and other fusidane antibiotics remain obscure. During product characterization of oxidosqualene cyclases; in Aspergillus fumigatus, we found the long-sought cyclase that makes (17Z)-protosta-17(20),24-dien-3 beta-ol, the precursor of helvolic acid. We then identified a gene cluster encoding the pathway to helvolic acid, which is controlled by a transcription regulator (LaeA) associated with fungal virulence. Evidence regarding the evolutionary origin and taxonomic distribution of fusidane biosynthesis is also presented.
• Mitsuguchi, Hisashi; Seshime, Yasuyo; Fujii, Isao, <hi>Journal of the American Chemical Society</hi>, <hi>2009</hi>, vol. 131, p. 6402 - 6411
  作者：Mitsuguchi, Hisashi、Seshime, Yasuyo、Fujii, Isao、Shibuya, Masaaki、Ebizuka, Yutaka、Kushiro, Tetsuo

  DOI：——

  日期：——