(6b)-6-氢过氧基-胆甾-4-烯-3-酮 | 2207-76-3

• 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
• 中文名称: (6b)-6-氢过氧基-胆甾-4-烯-3-酮
• 英文名称: cholest-4-ene-6β-hydroperoxy-3-one
• 英文别名: 6β-hydroperoxy-cholest-4-en-3-one；6β-Hydroperoxy-cholest-4-en-3-on；6beta-Hydroperoxycholest-4-en-3-one；(6R,8S,9S,10R,13R,14S,17R)-6-hydroperoxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 2207-76-3
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: CVJNCIPPOLWWCO-ZAAZJSNSSA-N

物化性质

• 沸点：
  474.91°C (rough estimate)
• 密度：
  1.0362 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6b)-6-氢过氧基-胆甾-4-烯-3-酮 生成 4-胆甾烯-6-醇-3-酮
  参考文献：
  名称：

  DANG, HAI-SHAN;DAVIES, ALWYN G.;SCHIESSER, CARL H., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 789-794

  摘要：

  DOI：
• 作为产物：
  描述：

  5-胆甾烯-3-酮 在 氧气 、 苯 作用下， 生成 (6b)-6-氢过氧基-胆甾-4-烯-3-酮
  参考文献：
  名称：

  Schenck et al., Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 46,52

  摘要：

  DOI：

文献信息

• Isomerization, But Not Oxidation, Is Suppressed by a Single Point Mutation, E361Q, in the Reaction Catalyzed by Cholesterol Oxidase
  作者：Nicole S. Sampson、Ignatius J. Kass

  DOI：10.1021/ja962258o

  日期：1997.2.1

  The putative active site base of cholesterol oxidase from Streptomyces has been removed by site-directed mutagenesis and the mutant enzyme characterized. When glutamate-361 is mutated to a glutamine, the isomerization chemistry catalyzed by cholesterol oxidase is suppressed and the intermediate cholest-5-ene-3 one is isolated. The specific activity for oxidation is 20-fold slower than the wild-type reaction;though the specific activity for isomerization is 10 000-fold slower. Furthermore, incubation of cholest-5-ene-3-one with the E361Q cholesterol oxidase resulted in the production of cholest-4-ene-6 beta-hydroperoxy-3-one (6%), cholest-4-ene-3,6-dione (32%), cholest-4-ene-6 beta-ol-3-one (36%), and cholest-4-ene-6 alpha-hydropesoxy-3-one/cholest-4-ene-6 alpha-ol-3-one (13%), in addition to cholest-4-ene-3-one (13%). Measurement of reaction Stoichiometry eliminated the possibility that H2O2 or the C4a-hydroperoxy flavin was the oxygenation agent. It is proposed that cholest-4-ene-6-hydroperoxy-3-one is the product of radical chain autoxidation and that cholest-4-ene-3,6-dione and cholest-4-ene-6-ol-3-one are decomposition products of the hydroperoxy steroid radical. The characterization of the E361Q mutant chemistry has illuminated the importance of intermediate sequestration in enzyme catalysis. The mutant enzyme will be used to obtain information about the structure of the enzyme in the presence of the reaction intermediate. Moreover, the altered activity of E361Q cholesterol oxidase will facilitate its application in studies of cell membranes.
• Fieser et al., Journal of the American Chemical Society, 1955, vol. 77, p. 3928
  作者：Fieser et al.

  DOI：——

  日期：——
• US5929062A
  申请人：——

  公开号：US5929062A

  公开（公告）日：1999-07-27
• Schenck et al., Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 46,52
  作者：Schenck et al.

  DOI：——

  日期：——
• DANG, HAI-SHAN;DAVIES, ALWYN G.;SCHIESSER, CARL H., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 789-794
  作者：DANG, HAI-SHAN、DAVIES, ALWYN G.、SCHIESSER, CARL H.

  DOI：——

  日期：——