Chemical and Pharmaceutical Bulletin p. 1125 - 1129 (1992)
Update date:2022-08-05
Topics:
Tanimoto
Tsujikawa
Koizumi
Three positional isomers of diglucosyl-cyclomaltohexaose (diglucosyl-cG6) were chemically synthesized via 61,62-, 61,63-, and 61,64-di-O-(tert-butyldimethylsilyl)-cG6s (1, 2, and 3) prepared regiospecifically. Glucosylation of bis(2,3-di-O-acetyl)tetrakis(2,3,6-tri-O-acetyl)-cG6s obtained from the three regioisomeric compounds 1, 2, and 3 with 2,3,4,6-tetra-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyranose, followed by debenzylation and then deacetylation, afforded 61,62-, 61,63-, and 61,64-di-O-(α-D-glucopyranosyl)-cG6s (10, 11, and 12) together with configurational isomers. The desired compounds 10, 11, and 12 containing two (1 → 6)-α-linkages were isolated from the mixtures of their configurational isomers by high performance liquid chromatography. The three diglucosyl-cG6s synthesized chemically were used as authentic samples to identify the components in a mixture of diglucosyl-cG6s produced by an enzymatic process.
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