Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus tamarii KITA: transformation of a series of cortical steroid analogues

Hunter, A.C. and Carragher, N.E. (2003) Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus tamarii KITA: transformation of a series of cortical steroid analogues The journal of steroid biochemistry and molecular biology, 87 (4-5). pp. 301-308. ISSN 0960-0760

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Official URL: http://dx.doi.org/10.1016/j.jsbmb.2003.10.001

Abstract

A range of cortical steroids have been transformed by the fungusAspergillus tamarii, which has the ability to convert progesterone to testololactone in high yield through a four step enzymatic pathway. 16α,17α-Epoxyprogesterone underwent a rare epoxide opening resulting in a unique inversion of stereochemistry to give 16β-hydroxy-17α-oxa-Image-homo-androst-4-en-3,17-dione. The metabolism of deoxycorticosterone resulted in relatively efficient transformation to testololactone with no other products isolated. Transformation of 17α-hydroxyprogesterone yielded 17α-oxa-Image-homo-androst-1,4-dien-3,17-dione, a lactone not previously isolated from A. tamarii. Cortexolone was transformed to the 20(R)-alcohol with no further transformation observed. Evidence is also presented for the presence of a highly flexible but stereospecific keto-reductase. All metabolites were isolated by column chromatography and were identified by 1H, 13C NMR, DEPT analysis and other spectroscopic data.

Item Type:Journal article
Uncontrolled Keywords:Biotransformation; Aspergillus tamarii; Baeyer–Villiger oxidation; Lactonisation; Steroid; Cortical steroid; Epoxide opening; Progesterone
Subjects:A000 Medicine
C000 Biological and Biomedical Sciences > C700 Molecular Biology, Biophysics and Biochemistry
DOI (a stable link to the resource):10.1016/j.jsbmb.2003.10.001
Faculties:Faculty of Science and Engineering > School of Pharmacy and Biomolecular Sciences
ID Code:671
Deposited By:editor spbs
Deposited On:08 Nov 2007
Last Modified:18 Jun 2010 12:29

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