Preparation of three positional isomers of diglucosyl-cyclomaltohexaose.
Three positional isomers of diglucosyl-cyclomaltohexaose (diglucosyl-cG6) were chemically synthesized via 6(1),6(2)-, 6(1),6(3)-, and 6(1),6(4)-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-alpha-D-glucopyran ose, followed by debenzylation and then deacetylation, afforded 6(1),6(2)-, 6(1),6(3)-, and 6(1),6(4)-di-O-(alpha-D-glucopyranosyl)-cG6S (10, 11, and 12) together with configurational isomers. The desired compounds 10, 11, and 12 containing two (1----6)-alpha-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.
Tanimoto
T
T
Faculty of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya, Japan.
Tsujikawa
J
J
Koizumi
K
K
D002240:Carbohydrate Sequence; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D008969:Molecular Sequence Data; D047391:alpha-Cyclodextrins
D003505:Cyclodextrins; D047391:alpha-Cyclodextrins; C076912:diglucosyl-cyclomaltohexaose; C032613:alpha-cyclodextrin