Kolet Swati P, Haldar Saikat, Niloferjahan Siddiqui, Thulasiram Hirekodathakallu V
Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India; CSIR-Institute of Genomics and Integrative Biology, Mall Road, New Delhi 110007, India.
Steroids. 2014 Jul;85:6-12. doi: 10.1016/j.steroids.2014.04.002. Epub 2014 Apr 18.
Transformation of testosterone and progesterone into synthetically challenging 14α-hydroxy derivatives was achieved by using fungal strain Mucor hiemalis. Prolonged incubation led to the formation of corresponding 6β/7α,14α-dihydroxy metabolites. The position and stereochemistry of newly introduced hydroxyl group was determined by detailed spectroscopic analyses. The time course experiment indicated that fungal strain initiated transformation by hydroxylation at 14α-position followed by at 6β- or 7α-positions. Studies using cell-free extracts suggest that the 14α-hydroxylase activity is NADPH dependent and belongs to the cytochrome P450 family.
通过使用毛霉属真菌菌株Mucor hiemalis，实现了将睾酮和孕酮转化为合成上具有挑战性的14α-羟基衍生物。长时间孵育导致形成相应的6β/7α,14α-二羟基代谢物。通过详细的光谱分析确定了新引入羟基的位置和立体化学。时间进程实验表明，该真菌菌株通过在14α位羟基化，随后在6β-或7α-位羟基化来启动转化。使用无细胞提取物的研究表明，14α-羟化酶活性依赖于NADPH，属于细胞色素P450家族。
