6-Α-羟基地塞米松 | 111897-35-9

• 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
• 中文名称: 6-Α-羟基地塞米松
• 英文名称: 6alpha-Hydroxydexamethasone
• 英文别名: (6S,8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-6,11,17-trihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
• CAS: 111897-35-9
• 化学式: C₂₂H₂₉FO₆
• 分子量: 408.467
• InChiKey: RVBSTEHLLHXILB-GQKYHHCASA-N

物化性质

• 沸点：
  613.2±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  7

ADMET

代谢

6-α-羟基地塞米松是地塞米松的人类已知代谢物。

6-alpha-OH DEXAMETHASONE is a known human metabolite of dexamethasone.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  地塞米松 在 Bacillus megaterium DSM₃₁₉ CYP₁₀₆A₁ 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 以37%的产率得到
  参考文献：
  名称：

  Identification of new substrates for the CYP106A1-mediated 11-oxidation and investigation of the reaction mechanism

  摘要：

  CYP106A1 from Bacillus megaterium DSM319 was recently shown to catalyze steroid and terpene hydroxylations. Besides producing hydroxylated steroid metabolites at positions 6β, 7β, 9α and 15β, the enzyme displayed previously unknown 11‐oxidase activity towards 11β‐hydroxysteroids. Novel examples for 11‐oxidation were identified and confirmed by 1H and 13C NMR for prednisolone, dexamethasone and 11β‐hydroxyandrostenedione. However, only 11β‐hydroxyandrostenedione formed a single 11‐keto product. The latter reaction was chosen to investigate the kinetic solvent isotope effect on the steady‐state turnover of the CYP106A1‐mediated 11‐oxidation. Our results reveal a large inverse kinetic isotope effect (∼0.44) suggesting the involvement of the ferric peroxoanion as a reactive intermediate.

  DOI：

  10.1016/j.febslet.2015.07.011

文献信息

• Identification of new substrates for the CYP106A1-mediated 11-oxidation and investigation of the reaction mechanism
  作者：Flora Marta Kiss、Yogan Khatri、Josef Zapp、Rita Bernhardt

  DOI：10.1016/j.febslet.2015.07.011

  日期：2015.8.19

  CYP106A1 from Bacillus megaterium DSM319 was recently shown to catalyze steroid and terpene hydroxylations. Besides producing hydroxylated steroid metabolites at positions 6β, 7β, 9α and 15β, the enzyme displayed previously unknown 11‐oxidase activity towards 11β‐hydroxysteroids. Novel examples for 11‐oxidation were identified and confirmed by 1H and 13C NMR for prednisolone, dexamethasone and 11β‐hydroxyandrostenedione. However, only 11β‐hydroxyandrostenedione formed a single 11‐keto product. The latter reaction was chosen to investigate the kinetic solvent isotope effect on the steady‐state turnover of the CYP106A1‐mediated 11‐oxidation. Our results reveal a large inverse kinetic isotope effect (∼0.44) suggesting the involvement of the ferric peroxoanion as a reactive intermediate.