Ambrus G, Jekkel A, Ilköy E, Horváth G, Böcskei Z
Institute for Drug Research, Budapest, Hungary.
Steroids. 1995 Sep;60(9):626-9. doi: 10.1016/0039-128x(95)00078-5.
In order to investigate the effect of the different stereochemistry of C-24 on the microbial C-26 oxidation of sterol side-chain the genetically modified Mycobacterium sp. BCS 396 strain was used to transform erogsterol. Ergosterol was converted to 3-oxo-4,22-ergostadien-26-oic acid methyl ester, 3-oxo-1,4,22-ergostatrien-26-oic acid methyl ester, and 3-oxo-1,4,22-ergostatrien-26-oic acid, the structures of which have been determined by IR, 1H NMR, 13C NMR, and mass spectroscopy. The X-ray structure of 3-oxo-4,22-ergostadien-26-oic acid methyl ester revealed that oxidation at C-26 of the ergostane side-chain generates a chiral center with S-configuration at C-25 as a result of chiral induction of the C-24 center.
为了研究C-24不同立体化学对甾醇侧链微生物C-26氧化的影响，使用基因工程改造的分枝杆菌属BCS 396菌株对麦角甾醇进行转化。麦角甾醇被转化为3-氧代-4,22-麦角甾二烯-26-酸甲酯、3-氧代-1,4,22-麦角甾三烯-26-酸甲酯和3-氧代-1,4,22-麦角甾三烯-26-酸，其结构已通过红外光谱、1H核磁共振、13C核磁共振和质谱确定。3-氧代-4,22-麦角甾二烯-26-酸甲酯的X射线结构表明，由于C-24中心的手性诱导作用，麦角甾烷侧链C-26处的氧化在C-25处产生了一个具有S-构型的手性中心。
