Mucor hiemalis mediated 14alpha-hydroxylation on steroids: In vivo and in vitro investigations of 14alpha-hydroxylase activity

摘要

Transformation of testosterone and progesterone into synthetically challenging 14a-hydroxy derivatives was achieved by using fungal strain Mucor hiemalis. Prolonged incubation led to the formation of corresponding 6beta/7alpha, 14alpha-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 14alpha-position followed by at 6beta- or 7alpha-positions. Studies using cell-free extracts suggest that the 14alpha-hydroxylase activity is NADPH dependent and belongs to the cytochrome P450 family.