PMID: 9185296Jun 1, 1997Paper

A direct stereoselective synthesis of 7 beta-hydroxytestosterone

Steroids
D LabareeR B Hochberg

Abstract

Although 7 beta-hydroxytestosterone is a known product of hepatic androgen metabolism, there are no published methods for its chemical synthesis except from the equally difficult to obtain 7 beta-hydroxy-4-androstene-3,17-dione. We found that several seemingly straightforward routes for its synthesis failed. Consequently, we tried to produce 7 beta-hydroxytestosterone by enzymatic oxidation of 5-androstene-3 beta, 7 beta, 17 beta-triol with cholesterol oxidase (Brevibacterium sp.), a procedure previously used to synthesize 7 beta-hydroxy-4-cholesten-3-one from 3 beta, 7 beta-dihydroxycholesterol (Alexander and Fisher 1995). However, 5-androstene-3 beta, 7 beta, 17 beta-triol was, at best, a very poor substrate for the enzyme leading to the production of 7 beta-hydroxytestosterone in only trace amounts. Thus, we explored a strategy for the enzymatic synthesis in which a C8-ester at C-17 (5-androstene-3 beta, 7 beta, 17 beta-triol 17-caprylate) would serve to mimic the bulky and hydrophobic side chain of cholesterol and thus allow the C19-steroid to act as an effective substrate. When this ester was incubated with cholesterol oxidase, it was converted efficiently to 7 beta-hydroxytestosterone-17-caprylate. Attempts to remove the ...Continue Reading

Citations

May 21, 2005·Journal of Pharmaceutical and Biomedical Analysis·Tatsuya HigashiKazutake Shimada
Jun 12, 2003·Steroids·Evaggelia S ArsenouSotiris S Nikolaropoulos
Jul 18, 2008·Molecular BioSystems·Jesús F Aparicio, Juan F Martín
Jun 27, 2014·Mass Spectrometry Reviews·Man Ho Choi, Bong Chul Chung
Nov 26, 2009·American Journal of Physical Anthropology·Adam VeroniMichael A Schillaci
Oct 22, 2009·The FEBS Journal·Loredano PollegioniGianluca Molla
Nov 4, 2004·Journal of Pharmaceutical and Biomedical Analysis·Tatsuya HigashiKazutake Shimada
Jul 15, 2015·Applied Microbiology and Biotechnology·Mathias PicklKurt Faber
Jan 21, 2010·Cancer Epidemiology, Biomarkers & Prevention : a Publication of the American Association for Cancer Research, Cosponsored by the American Society of Preventive Oncology·Ju-Yeon MoonMan Ho Choi
Jun 4, 1999·Journal of Medicinal Chemistry·D C LabareeR B Hochberg

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