Rhodococcus erythropolis

• 英文名称: Rhodococcus erythropolis

反应信息

• 作为试剂：
  描述：

  地诺孕素 在 phosphate buffer 、 Rhodococcus erythropolis 作用下， 以 二甲基亚砜 为溶剂， 生成 地诺孕素EP杂质H 、 ?9,11-去氢-17alpha-氰基甲基雌二醇 、 2-((8R,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-acetamide 、 17α-acetamido-estra-1,3,5(10),9(11)-tetraene-3,17β-diol
  参考文献：
  名称：

  Nitrile hydratase from Rhodococcus erythropolis: Metabolization of steroidal compounds with a nitrile group

  摘要：

  The progestin dienogest (17 alpha-cyanomethyl-17 beta-hydroxy-estra-4,9-dien-3-one) was metabolized by the nitrile hydratase-containing microorganism Rhodococcus erythropolis. An enzymatic hydrolysis of the nitrile group at the 17 alpha-side chain was intended to obtain novel derivatives and to test them for progesterone receptor affinity. In contrast to the rapid enzymatic hydrolysis of nonsteroidal nitriles, the nitrile group of dienogest was cleaved very slowly. The dominant reaction was an aromatization of ring A. After prolonged fermentation, the 17 alpha-acetamido derivatives of estradiol and of 9(11)-dehydroestradiol were formed. Three of the metabolites were also prepared synthetically. They were tested for hormonal activity by assessing their binding to progesterone and estrogen receptors in vitro. Neither the aromatized 17 alpha-acetamido derivatives nor the dienogest derivative 17 alpha-acetamido-17 beta-hydroxy-estra-4,9-dien-3-one, which was prepared synthetically only, exhibited affinity for the progesterone receptor. (C) 1999 Elsevier Science Inc. All fights reserved.

  DOI：

  10.1016/s0039-128x(99)00028-8