5 alpha -ANDROSTANE-3,2 prime -OXIRANE.

Charles L Bevins, Shanta Bantia, Ralph M. Pollack, Patricia L. Bounds, Robert H. Kayser

Research output: Contribution to journalArticlepeer-review

27 Scopus citations


The affinity label (3S)-spiro left bracket 5 alpha -androstane-3,2 prime -oxirane right bracket -17 beta -ol (1 beta ) inhibits 3-oxo- DELTA **5-steroid isomerase with a stoichiometry of one molecule of inhibitor to one enzyme monomer. The trypsin digest of the inhibited enzyme shows two distinct steroid-bound peptides, both of which are derived from residues 14-45 of the enzyme. The two modified peptides (TPS//1 and TPS//2) were isolated by HPLC, and each was shown to have an ester bond linking the steroid to the peptide fragment. Hydrolysis of each of the two peptide-steroid adducts releases a different steroid. TPS//1 gives 3 alpha -(hydroxymethyl)-5 alpha -androstane-3 beta ,17 beta -diol (S//1) whereas TPS//2 releases 3 beta -(hydroxymethyl)-5 alpha -androstane-3 alpha ,17 beta -diol (S//2).

Original languageEnglish (US)
Pages (from-to)4957-4962
Number of pages6
JournalJournal of the American Chemical Society
Issue number17
StatePublished - Jan 1 1984
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)


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