Transformations of acyclic isoprenoids by Aspergillus niger: selective oxidation of ω-methyl and remote double bonds

Abstract

A strain of Aspergillus niger was used to study the mode of biotransformation of various acyclic isoprenoids. The organism showed ability to carry out the oxidation of the ω-methyl and the remote double bond regio-and stereospecifically, resulting in the formation of ω-methyl hydroxylated and vicinal trans-diols in all the compounds tested (I-VII). However, these two activities seem to have preferential structural requirements. When an acyclic isoprenoid with a ketone functionality such as geranylacetone was used as the substrate, the organism also carried out asymmetric reduction of the keto group.