The microbiological hydroxylation of steroids and related compounds

Abstract

The factors which determine the specific positions at which steroids are hydroxylated by micro-organisms are being investigated, using mono-ketones or keto-alcohols of the androstane series as substrates and infra-red and n.m.r. spectroscopy to determine the structures of the products. Whereas the major product of the hydroxylation of 5α-androstan-3-one by cultures of Calonectria decora is 12β,15α-dihydroxy-5α-androstan-3-one, by contrast, with the 17-ketone as substrate, 1 β,6α-dihydroxylation occurs. The hydroxyl groups introduced are on centres about 4 A apart and at distances from the carbonyl ‘directing7 group which are approximately comparable. With a range of other substrates and with several other organisms results of a similar nature are obtained, revealing the dependence of the substitution pattern on the position of the oxygen function(s) of the substrate. © 1973, Walter de Gruyter. All rights reserved.