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Synthesis of a novel vitamin E derivative, 2‐(α‐ d ‐glucopyranosyl)methyl‐2,5,7,8‐tetramethylchroman‐6‐ol, by α‐glucosidase‐catalyzed transglycosylation
Author(s) -
Murase Hironobu,
Yamauchi Ryo,
Kato Koji,
Kunieda Tsutomu,
Terao Junji
Publication year - 1997
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-997-0011-6
Subject(s) - chemistry , trolox , maltose , glucoside , derivative (finance) , antioxidant , stereochemistry , organic chemistry , dpph , sucrose , medicine , alternative medicine , pathology , economics , financial economics
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 α‐glucosidase from Saccharomyces species. The glycosylated product was identified as 2‐(α‐ d ‐glucopyranosyl)methyl‐2,5,7,8,‐tetramethylchroman‐6‐ol (TMG) by mass spectrometry and nuclear magnetic resonance spectroscopy. The optimal pH of transglycosylation was 5.5, and the yield of TMG increased as the concentration of maltose increased. IMG has high solubility in water (>1×10 3 mg/mL). The 1,1‐diphenyl‐2‐picrylhydrazyl radical scavenging activity of TMG was found to be nearly the same as those of α‐tocopherol, Trolox (2‐carboxy‐2,5,7,8‐tetramethylchroman‐6‐ol), and ascorbic acid.