Glucosylation of benzyl alcohols by the cultured suspension cells of Nicotiana tabacum and Catharanthus roseus

The cultured cells of Nicotiana tabacum (white cells) converted regioselect ively exogenous 2-, 3-, and 4-hydroxybenzyl alcohols into corresponding hyd roxybenzyl-beta-D-glucopyranoside. (RS)-1-Phenylethanol having chiral cente r in its substituent was also glucosylated to give 1-phenylethyl-beta-D-glu copyranoside by the cultured cells of N. tabacum (white and green cells) an d Catharanthus roseus. The glucosylation with the green cells of N. tabacum occurred enantioselectively to give the glucoside of (S)-alcohol preferent ially, while the glucosylation with the white cells of N. tabacum and the C . roseus cells gave preferentially the glucoside of (R)-alcohol. (C) 1999 E lsevier Science B.V: All rights reserved.