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.
• Effects of Alternative Redox Partners and Oxidizing Agents on CYP154C8 Catalytic Activity and Product Distribution
  作者：Bikash Dangi、Hyun Park、Tae-Jin Oh

  DOI：10.1002/cbic.201800284

  日期：2018.11.2

  Altered catalytic activity was displayed by CYP154C8 reconstituted with variant redox partners. In addition to 16α‐hydroxylation, progesterone and 11‐oxoprogesterone also underwent 6β‐hydroxylation in reactions supported by diacetoxyiodobenzene (PIDA) in a way not previously observed with either NADPH‐ or NADH‐dependent systems. CYP154C8 also showed conversion of steroids at high concentrations of

  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。