Enzymic hydroxylation and sulfoxidation of cyclopropyl compounds by fungal biotransformation

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Abstract
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.