Hydroxylation of 6β-methoxy-3α,5-cyclo-5α-androstan-17-one with Rhizopus nigricans

Thoa, Huynh Kim; Procházka, Ž.; Budêšínský, Miloś; Kočovský, Pavel

doi:10.1135/cccc19782305

Cited by 7 publications

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“…Migration of double bonds adjacent to the reactive centre has been observed during enzymic hydroxylation of terpenes (4) and steroids (5), and attributed to allylic rearrangement of a carbon radical intermediate. Fungal hydroxylation or sulfoxidation adjacent to a cyclopropyl ring has not been reported, however; the cyclopropyl-containing steroids that have been used as substrates for fungal biotransformation are hydroxylated at sites remote from the cyclopropyl functionality (6).…”

Section: Introductionmentioning

confidence: 99%

Enzymic hydroxylation and sulfoxidation of cyclopropyl compounds by fungal biotransformation

Holland¹,

Chernishenko²,

Conn³

et al. 1990

Can. J. Chem.

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A series of compounds containing a cyclopropyl ring adjacent to the position of oxidation during fungal biotransformation has been prepared and subjected to enzymic oxidation using Mortierellaisabellina or Rhizopusarrhizus. Carbon hydroxylation and sulfoxidation reactions were observed, but in neither case did opening of the cyclopropyl ring occur. Both these reactions were subject to inhibition by carbon monoxide but not by cyanide ion, properties characteristic of cytochrome P-450 dependent mono-oxygenase enzymes. Hydroxylation at a cyclopropyl C—H bond has been studied by the use of phenylcyclopropane and phenylthiirane as substrates for the mono-oxygenase of M. isabellina. The former was not oxidized, but the latter was converted to phenyl glyoxylic acid in moderate yield. Keywords: biotransformation, cyclopropanes, fungi, metabolism.

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Section: Introductionmentioning

confidence: 99%