(20R)-protosta-13(17),24-dien-3β-ol

• 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: (20R)-protosta-13(17),24-dien-3β-ol
• 英文别名: 20(R)-protosta-13(17),24-dien-3β-ol；protosta-13(17),24-dien-3β-ol；3β-Hydroxy-protosta-13(17),24-dien；(3S,5R,8S,9S,10R,14R)-4,4,8,10,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: ISSSGGUZUSDMCE-LOCHZAJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  31
• 可旋转键数：
  4
• 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

• 作为产物：
  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：

文献信息

• The cysteine 703 to isoleucine or histidine mutation of the oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae generates an iridal-type triterpenoid
  作者：Cheng-Hsiang Chang、Yi-Chi Chen、Sheng-Wei Tseng、Yuan-Ting Liu、Hao-Yu Wen、Wen-Hsuan Li、Chiao-Ying Huang、Cheng-Yu Ko、Tsai-Ting Wang、Tung-Kung Wu

  DOI：10.1016/j.biochi.2012.06.014

  日期：2012.11

  generates an unusual truncated bicyclic rearranged intermediate, (8R,9R,10R)-polypoda-5,13E,17E,21-tetraen-3β-ol, related to iridal-skeleton triterpenoid. Numerous oxidosqualene-cyclized truncated intermediates, including tricyclic, unrearranged tetracyclic with 17α/β exocyclic hydrocarbon side chain, rearranged tetracyclic, and chair-chair-chair tricyclic intermediates (compounds 3-9), were also isolated

  啤酒酵母氧化角鲨烯-羊毛甾醇环化酶ERG7（ERG7（C703I / H））中Cys703到Ile或His突变产生不寻常的截短的双环重排中间体，（8R，9R，10R）-polypoda-5,13E，17E，21-tetraenen -3β-ol，与虹膜骨架三萜有关。还从ERG7（C703X）位点分离出许多氧化性角鲨烯环化的截短的中间体，包括三环，带有17α/β外环烃侧链的未重排四环，重排四环和椅-椅-三环中间体（化合物3-9）。饱和突变或ERG7（F699T / C703I）双重突变，表明Cys703残基在稳定双环C-8阳离子和重排的中间体或与Phe699相互作用中的功能，并为工程化ERG7生产生物活性物质开辟了一条新途径代理商。
• 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