Predominant allyic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor Tauricus IMI23312

Hunter, A.C., Mills, P.W., Dedi, C. and Dodd, H.T. (2008) Predominant allyic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor Tauricus IMI23312 Journal of Steroid Biochemistry and Molecular Biology, 180 (1-2). pp. 155-163. ISSN 0960-0760

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Abstract

This paper demonstrates for the first time transformation of a series of steroids (progesterone, androst-4-en-3,17-dione, testosterone, pregnenolone and dehydroepiandrosterone) by the thermophilic fungus Rhizomucor tauricus. All transformations were found to be oxidative (monohydroxylation and dihydroxylation) with allylic hydroxylation the predominant route of attack functionalizing the steroidal skeleta. Timed experiments demonstrated that dihydroxylation of progesterone, androst-4-en-3,17-dione and pregnenolone all initiated with hydroxylation on ring-B followed by attack on ring-C. Similar patterns of steroidal transformation to those observed with R. tauricus have been observed with some species of thermophilic Bacilli and mesophilic fungi. All metabolites were isolated by column chromatography and were identified by 1H, 13C NMR, DEPT analysis and other spectroscopic data. The application of thermophilic fungi to steroid transformation may represent a potentially rich source for the generation of new steroidal compounds as well as for uncovering inter and intraspecies similarities and differences in steroid metabolism.

Item Type: Journal article
Uncontrolled Keywords: Rhizomucor tauricus; Allylic oxidation; Steroid transformation; Thermophilic fungus; Hydroxylation
Subjects: F000 Physical Sciences > F100 Chemistry
C000 Biological and Biomedical Sciences > C700 Molecular Biology, Biophysics and Biochemistry
DOI (a stable link to the resource): 10.1016/j.jsbmb.2007.09.022
Faculties: Faculty of Science and Engineering > School of Pharmacy and Biomolecular Sciences > Chemical Biology
Depositing User: editor spbs
Date Deposited: 12 Mar 2008
Last Modified: 01 May 2012 14:46
URI: http://eprints.brighton.ac.uk/id/eprint/4725

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