3α,11α,17β-trihydroxy-5α-androstane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3α,11α,17β-trihydroxy-5α-androstane
• 英文别名: 5α-androstane-3α,11α,17β-triol；5-Alpha-androstan-3-alpha,11-alpha,17-beta-triol；(3R,5S,8S,9S,10S,11R,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11,17-triol
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: FNICIUSFFWRLFW-JKMQGDIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5a-雄甾烷-3a,17b-二醇 在 Beauveria bassiana KCH 1065 作用下， 以 丙酮 为溶剂， 反应 9.0h， 以8%的产率得到3,7-二羟基雄甾烷-17-酮
  参考文献：
  名称：

  Microbial Baeyer–Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway

  摘要：

  Beauveria bassiana KCH 1065, as was recently demonstrated, is unusual amongst fungal biocatalysts in that it converts C-19 3-oxo-4-ene and 3 beta-hydroxy-5-ene as well as 3 beta-hydroxy-5 alpha-saturated steroids to 11 alpha-hydroxy ring-D lactones. The Baeyer-Villiger monooxygenase (BVMO) of this strain is distinguished from other enzymes catalyzing BVO of steroidal ketones by the fact that it oxidizes solely substrates with 11 alpha-hydroxyl group. The current study using a series of 5 alpha-saturated steroids (androsterone, 3 alpha-androstanediol and androstanedione) has highlighted that a small change of the steroid structure can result in significant differences of the metabolic fate. It was found that the 3 alpha-stereochemistry of hydroxyl group restricted "normal" binding orientation of the substrate within 11 alpha-hydroxylase and, as a result, androsterone and 3 alpha-androstanediol were converted into a mixture of 7 beta-, 11 alpha- and 7 alpha-hydroxy derivatives. Hydroxylation of androstanedione occurred only at the 11 alpha-position, indicating that the 3-oxo group limits the alternative binding orientation of the substrate within the hydroxylase. Only androstanedione and 3 alpha-androstanediol were metabolized to hydroxylactones. The study uniquely demonstrated preference for oxidation of equatorial (11 alpha-, 7 beta-) hydroxyketones by BVMO from B. bassiana. The time course experiments suggested that the activity of 17 beta-HSD is a factor determining the amount of produced ring-D lactones. The obtained 11 alpha-hydroxylactones underwent further transformations (oxy-red reactions) at C-3. During conversion of androstanedione, a minor dehydrogenation pathway was observed with generation of 11 alpha,17 beta-dihydroxy-5 alpha-androst-1-en-3-one. The introduction of C1-C2 double bond has been recorded in B. bassiana for the first time. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.006

文献信息

• Microbial transformation of androst-4-ene-3,17-dione by Beauveria bassiana
  作者：Zhigang Xiong、Qi Wei、Hanmei Chen、Shouwen Chen、Wenjin Xu、Guofu Qiu、Shucai Liang、Xianming Hu

  DOI：10.1016/j.steroids.2006.07.007

  日期：2006.11

  The microbial transformation of androst-4-ene-3,17-dione (I) by the fungus Beauveria bassiana CCTCC AF206001 has been investigated using pH 6.0 and 7.0 media. Two hydroxylated metabolites were obtained with the pH 6.0 medium. The major product was 11alpha-hydroxyandrost-4-ene-3,17-dione (II) whereas the minor product was 6beta,11alpha-dihydroxyandrost-4-ene-3,17-dione (III). On the other hand, four

  已经使用 pH 6.0 和 7.0 介质研究了真菌白僵菌 CCTCC AF206001 对雄激素-4-烯-3,17-二酮 (I) 的微生物转化。在 pH 6.0 介质中获得了两种羟基化代谢物。主要产物是 11alpha-hydroxyandrost-4-ene-3,17-dione (II) 而次要产物是 6beta,11alpha-dihydroxyandrost-4-ene-3,17-dione (III)。另一方面，在 pH 7.0 的介质中获得了四种羟基化和/或还原的代谢物。主要产品为11alpha,17beta-dihydroxyandrost-ene-3-one (V)，次要产品为17beta-hydroxyandrost-ene-3-one (IV), 6beta,11alpha,17beta-trihydroxyandrost-ene-3-one ( VI) 和 3alpha
• Microbial Baeyer–Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway
  作者：Alina Świzdor、Anna Panek、Natalia Milecka-Tronina

  DOI：10.1016/j.steroids.2014.01.006

  日期：2014.4

  Beauveria bassiana KCH 1065, as was recently demonstrated, is unusual amongst fungal biocatalysts in that it converts C-19 3-oxo-4-ene and 3 beta-hydroxy-5-ene as well as 3 beta-hydroxy-5 alpha-saturated steroids to 11 alpha-hydroxy ring-D lactones. The Baeyer-Villiger monooxygenase (BVMO) of this strain is distinguished from other enzymes catalyzing BVO of steroidal ketones by the fact that it oxidizes solely substrates with 11 alpha-hydroxyl group. The current study using a series of 5 alpha-saturated steroids (androsterone, 3 alpha-androstanediol and androstanedione) has highlighted that a small change of the steroid structure can result in significant differences of the metabolic fate. It was found that the 3 alpha-stereochemistry of hydroxyl group restricted "normal" binding orientation of the substrate within 11 alpha-hydroxylase and, as a result, androsterone and 3 alpha-androstanediol were converted into a mixture of 7 beta-, 11 alpha- and 7 alpha-hydroxy derivatives. Hydroxylation of androstanedione occurred only at the 11 alpha-position, indicating that the 3-oxo group limits the alternative binding orientation of the substrate within the hydroxylase. Only androstanedione and 3 alpha-androstanediol were metabolized to hydroxylactones. The study uniquely demonstrated preference for oxidation of equatorial (11 alpha-, 7 beta-) hydroxyketones by BVMO from B. bassiana. The time course experiments suggested that the activity of 17 beta-HSD is a factor determining the amount of produced ring-D lactones. The obtained 11 alpha-hydroxylactones underwent further transformations (oxy-red reactions) at C-3. During conversion of androstanedione, a minor dehydrogenation pathway was observed with generation of 11 alpha,17 beta-dihydroxy-5 alpha-androst-1-en-3-one. The introduction of C1-C2 double bond has been recorded in B. bassiana for the first time. (C) 2014 Elsevier Inc. All rights reserved.