Separation and characterization of five positional isomers of trimaltosyl-cyclomaltoheptaose (trimaltosyl-β-cyclodextrin)

✍ Scribed by Yasuyo Okada; Kyoko Koizumi; Sumio Kitahata

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 808 KB
• Volume: 254
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)84238-8

✦ Synopsis

Trace amounts of trimaltosyl-cyclomaltoheptaoses (trimaltosyl-fi-cyclodextrins, trhnaltosyl-@CDs) were found in a mixture of maltosyl-cyclomaltoheptaoses (maltosyl-/.%cyclodextrins, maltosyl-#ICDs) prepared from maltose and cyclomaltoheptaose (B-cyclodextrin, gCD) through the reverse action of KZebsieZla pneumoniae pullulanase. Five positional isomers of trimaltosyl-gCD were isolated by highperformance liquid chromatography (HPLC) on a reversed-phase column and a graphitixed carbon column. For the structural analysis of 6l, 6*, 63-, 6l, 6*, 65-, and 6l, 63, 65-tri-O-maltosyl-@CDs, an enxymic method using glucoamylolysis, followed by hydrolysis with Bacillus subtilLs saccharifying a-amylase, was applied. Although 6l, 6*, 64-and 6l, 6*, 66-substituted isomers were indistinguishable by this method, these isomers were distinguished clearly by digestion of branched oligosaccharides produced from each isomer by the aforesaid method, with B. sfearothernaophilus neopullulanase or with glucoamylase. The resulting hydrolysates were analyzed by HPLC on an amino derivatixed column and by fast-atom bombardment spectrometry (FABMS). The chromatographic behavior and spectral data (13C NMR and FABMS) of five positional isomers of trimaltosyl-pCD are described. * For a preliminary report, see ref 1.