3α,7β,17β-trihydroxy-5α-androstane | 41843-62-3

• 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,7β,17β-trihydroxy-5α-androstane
• 英文别名: Androstane-3,7,17-triol, (3alpha,5alpha,7beta,17beta)-；(3R,5R,7S,8R,9S,10S,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-3,7,17-triol
• CAS: 41843-62-3
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: UFGLFVVFQFFPSV-LNDQFOMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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 24.0h， 以12 mg的产率得到3α,11α-dihydroxy-5α-androstan-17-one
  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 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.