SYNTHESIS OF A NOVEL VITAMIN-E DERIVATIVE, OPYRANOSYL)METHYL-2,5,7,8-TETRAMETHYLCHROMAN-6-OL, BY ALPHA-GLUCOSIDASE-CATALYZED TRANSGLYCOSYLATION

A novel derivative of vitamin E, vitamin E glucoside, was synthesized from 2-hydroxymethyl-2,5,7,8-tetramethylchroman-6-ol and maltose in a solution containing DMSO by transglycosylation with a-glucosidase from Saccharomyces species. The glycosylated product was identified as cop yranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol (TMC) by mass spectrom etry and nuclear magnetic resonance spectroscopy. The optimal pH of tr ansglycosylation was 5.5, and the yield of TMG increased as the concen tration of maltose increased. TMG has high solubility in water (>1 x 1 0(3) mg/mL). The 1,1-diphenyl-2-picrylhydrazyl radical scavenging acti vity of TMG was found to be nearly the same as those of alpha-tocopher ol, Trolox (2-carboxy-2,5,7,8-tetramethylchroman-6-ol), and ascorbic a cid.