Synthesis of a novel vitamin E derivative, 2-(α-d-glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol, by α-glucosidase-catalyzed transglycosylation |
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| Authors: | Hironobu Murase Ryo Yamauchi Koji Kato Tsutomu Kunieda Junji Terao |
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| Affiliation: | (1) The United Graduate School of Agricultural Sciences, Gitu University, 501-11 Gifu, Japan;(2) National Food Research Institute, Ministry of Agriculture, Forestry and Fisherles, 305 Ibaraki, Japan;(3) CCI Corporation, 12 Shinhazama, 501-32 Seki City, Gifu, Japan |
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| Abstract: | 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 (>1×103 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. |
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