Preparation of three positional isomers of diglucosyl-cyclomaltohexaose

Article abstract of DOI:10.1248/cpb.40.1125

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.

Full text of DOI:10.1248/cpb.40.1125

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service