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

Hunter, A Christy, Mills, Paul W, Dedi, Cinzia and Dodd, Howard T (2008) Predominant allylic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor tauricus IMI23312. The Journal of Steroid Biochemistry and Molecular Biology, 108 (1-2). pp. 155-163. ISSN 0960-0760

Full content URL: https://doi.org/10.1016/j.jsbmb.2007.09.022

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Item Type:Article
Item Status:Live Archive

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.

Keywords:Rhizomucor tauricus, Allylic oxidation, Steroid transformation, Thermophilic fungus, Hydroxylation
Divisions:College of Science > School of Pharmacy
ID Code:45445
Deposited On:13 Jul 2021 12:43

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