化学学报 ›› 2001, Vol. 59 ›› Issue (4): 604-609. 上一篇    下一篇

研究论文

18-甲基腺甾烯酮一类物的酶催化羟化

周维善;蔡峰;沈季铭   

  1. 中国科学院上海有机化学研究所.上海(200032)
  • 发布日期:2001-04-15

Enzymatic hydroxylation of 18-methylgona-4-en-3-one

Zhou Weishan;Cai Feng;Shen Jiming   

  1. Shanghai Inst Organ Chem., CAS.Shanghai(200032)
  • Published:2001-04-15

18-甲基-11α-羟基腺甾-4-烯-3,17-双酮是合成高效口服避孕药的重要中间体。试用黑根霉酶羟化引进11α-羟基于18-甲基-19-失碳雌甾-4-烯-3,17-双酮,得到包括该化合物在内的几种不同位置羟基产物的混合物。改用赭曲霉酶羟化同一底物也得到包括11α-羟基在内的几种不同位置羟基产物的混合物。而用赭曲霉催化羟化18-甲基-17β-羟基腺甾-4-烯-3-酮时,首次得到15α-羟化的主要产物和7β羟化的次要产物。前者可用来合成另一类高效口服避孕药△^15-D-18-甲基炔诺酮。

关键词: 甾酮, 酶, 曲霉, 赭曲酶, 羟基化, 催化

18-methyl-11α-hydroxygona-4-en-3,17-dione is a very important intermediate of some highly effective oral contraceptives. 18 methylgona -4-en-3,17-dione was subjected to enzymatic hydroxylation by rhizopus nigricans to afford a mixture of some hydroxylated products including 11α-hydroxylated derivative. aspergillus ochroceus was also used for the same substrate to afford the similar results. 18-methy-17 β- hydroxygona-4-en-3-one was enzymaticly hydroxylated by Aspergillus ochraceus to yield 15α-hydroxylated derivative as the major product and 7β-hydroxylated derivative as a minor product. 15α-hydroylated derivative shich could be used for synthesis of an highly effective oral contraceptive Gestodene, was isolated from this microorganism for the first time.

Key words: STERONE, ENZYME, ASPERGILLUS SP, HYDROXYLATION, CATALYSIS

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