Efficient and selective glucosylation of prenylated phenolic compounds by Mucor hiemalis

A highly regio- and stereo-specific biocatalytic reaction to produce the glucosides of natural prenylated phenolic compounds by Mucor hiemalis CGMCC 3.14114 is described. M. hiemalis could efficiently catalyze beta-Omicron-glucosylation of the isoprenyl-neighboring hydroxyl group, rather than other hydroxyls with low steric hindrance. This reaction was demonstrated by 28 compounds with different basic skeletons. The conversion rate was above 90% for most compounds. Scaled-up biotransformations of 15 substrates yielded 17 products, including 12 new compounds. These products showed enhanced water solubility and improved intestinal absorption in a Caco-2 cell monolayer model. This reaction provides a facile and efficient approach to synthesize the glucosides of prenylated phenolics, which are rare in natural products.