title: Mucor hiemalis mediated 14α-hydroxylation on steroids: in vivo and in vitro investigations of 14α-hydroxylase activity.
abstract: 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.
authors.affiliation: Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
authors.forename: Swati P
authors.initials: SP
authors.lastname: Kolet
authors.affiliation: Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
authors.forename: Saikat
authors.initials: S
authors.lastname: Haldar
authors.affiliation: Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
authors.forename: Siddiqui
authors.initials: S
authors.lastname: Niloferjahan
authors.affiliation: 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. Electronic address: hv.thulasiram@ncl.res.in.
authors.forename: Hirekodathakallu V
authors.initials: HV
authors.lastname: Thulasiram
mesh_terms: D002474:Cell-Free System; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry* / Q000378:metabolism; D006900:Hydroxylation; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D009089:Mucor / Q000737:chemistry; D011374:Progesterone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry; D013739:Testosterone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013256:Steroids; D013739:Testosterone; D011374:Progesterone; D003577:Cytochrome P-450 Enzyme System
keywords: 14α-Hydroxylase; Biotransformation; Mucor hiemalis; Progesterone; Testosterone