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Steroidal Free Radicals as Possible Intermediates in the Biosynthesis of C19-△16-Steroids

By Violet Lippman and Seymour Lieberman

Abstract

Treatment of deoxycorticosterone with reagents that abstract a hydrogen atom from the C-21-hydroxyl group leads to the formation of androsta-4,16-dien-3-one. In vitro incubations of [1,2-3H]deoxycorticosterone with homogenates of boar testis tissue produce the tritiated dienone. This reaction can be formulated as an abstraction of hydrogen from the C-21-hydroxyl group to form a C-21-alkoxy radical, followed by a 1,5-H·shift from the C-16 atom and β-scission of the C-16-alkoxy radical leading to the loss of a C2 fragment (C-20 and C-21) with the formation of the double bond between C-16 and C-17

Topics: Biological Sciences: Biochemistry
Year: 1970
OAI identifier: oai:pubmedcentral.nih.gov:283423
Provided by: PubMed Central
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