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 journalArticle

27 Citations (Scopus)

Abstract

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
Volume106
Issue number17
StatePublished - Jan 1 1984
Externally publishedYes

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Ethylene Oxide
Peptides
Androstane-3,17-diol
Steroids
Enzymes
Steroid Isomerases
Affinity Labels
Peptide Fragments
Stoichiometry
Trypsin
Labels
Hydrolysis
Esters
Monomers
High Pressure Liquid Chromatography
Molecules
androstane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Bevins, C. L., Bantia, S., Pollack, R. M., Bounds, P. L., & Kayser, R. H. (1984). 5 alpha -ANDROSTANE-3,2 prime -OXIRANE. Journal of the American Chemical Society, 106(17), 4957-4962.

5 alpha -ANDROSTANE-3,2 prime -OXIRANE. / Bevins, Charles L; Bantia, Shanta; Pollack, Ralph M.; Bounds, Patricia L.; Kayser, Robert H.

In: Journal of the American Chemical Society, Vol. 106, No. 17, 01.01.1984, p. 4957-4962.

Research output: Contribution to journalArticle

Bevins, CL, Bantia, S, Pollack, RM, Bounds, PL & Kayser, RH 1984, '5 alpha -ANDROSTANE-3,2 prime -OXIRANE.', Journal of the American Chemical Society, vol. 106, no. 17, pp. 4957-4962.
Bevins CL, Bantia S, Pollack RM, Bounds PL, Kayser RH. 5 alpha -ANDROSTANE-3,2 prime -OXIRANE. Journal of the American Chemical Society. 1984 Jan 1;106(17):4957-4962.
Bevins, Charles L ; Bantia, Shanta ; Pollack, Ralph M. ; Bounds, Patricia L. ; Kayser, Robert H. / 5 alpha -ANDROSTANE-3,2 prime -OXIRANE. In: Journal of the American Chemical Society. 1984 ; Vol. 106, No. 17. pp. 4957-4962.
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