6β-hydroxypregn-4-ene-3,11,20-trione | 28449-15-2

• 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: 6β-hydroxypregn-4-ene-3,11,20-trione
• 英文别名: 6β-hydroxy-11-oxoprogesterone；6-Hydroxypregn-4-ene-3,11,20-trione；(6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-hydroxy-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• CAS: 28449-15-2
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: OQHBUJSFKDUFCW-VTPSHUEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-孕烯-3,11,20-三酮 在 碘苯二乙酸 、 cytochrome CYP₁₅₄C₈ 作用下， 以 aq. phosphate buffer 为溶剂， 反应 2.0h， 生成 6β-hydroxypregn-4-ene-3,11,20-trione 、 16α-hydroxy-11-oxoprogesterone
  参考文献：
  名称：

  替代氧化还原伙伴和氧化剂对CYP154C8催化活性和产物分布的影响

  摘要：

  CYP154C8与变体氧化还原伙伴重构后，催化活性发生了变化。除16α-羟基化作用外，孕酮和11-氧代戊二酮还通过二乙酰氧基碘苯（PIDA）支持的反应也经历了6β-羟基化作用，这是以前在NADPH或NADH依赖性系统中未曾观察到的。CYP154C8还显示了在高浓度的H 2 O 2和H 2 O 2耐受性下类固醇的转化。

  DOI：

  10.1002/cbic.201800284

文献信息

• Biocatalyst mediated production of 6β,11α-dihydroxy derivatives of 4-ene-3-one steroids
  作者：Swati P. Kolet、Siddiqui Niloferjahan、Saikat Haldar、Rajesh Gonnade、Hirekodathakallu V. Thulasiram

  DOI：10.1016/j.steroids.2013.08.004

  日期：2013.11

  Biotransformation of steroids with 4-ene-3-one functionality such as progesterone (I), testosterone (II), 17 alpha-methyltestosterone (III), 4-androstene-3,17-dione (IV) and 19-nortestosterone (V) were studied by using a fungal system belonging to the genera of Mucor (M881). The fungal system efficiently and quantitatively converted these steroids in regio- and stereo-selective manner into corresponding 6 beta,11 alpha-dihydroxy compounds. Time course experiments suggested that the transformation was initiated by hydroxylation at 6 beta- or 11 alpha-(10 beta-hydroxy in case of V) to form monohydroxy derivatives which upon prolonged incubation were converted into corresponding 613,11oc-dihydroxy derivatives. The fermentation studies carried out using 5 L table-top fermentor with substrates (I and II) clearly indicates that 6 beta,11 alpha-dihydroxy derivatives of steroids with 4-ene-3-one functionality can be produced in large scale by using M881. (C) 2013 Elsevier Ltd.