Isolation and characterization of two positional isomers of novel heterogeneous branched cyclomaltohexaoses (alpha-cyclodextrins) having a D-galactobiosyl residue on the side chain.
Transgalactosylated products, 2-O-alpha-D-galactobiosyl-cyclomaltohexaoses (alpha-cyclodextrins, alphaCDs), were synthesized by alpha-galactosidase from coffee bean using melibiose and alphaCD as a donor substrate and an acceptor, respectively. Two positional isomers of 2-O-alpha-galactobiosyl-alphaCDs were isolated and purified by HPLC, and their structures were elucidated by FABMS and NMR spectroscopies, as well as by an enzymatic degradation method. The chromatographic behavior of these novel galactosylated alphaCDs was compared on three HPLC columns with different separation modes.
Okada
Yasuyo
Y
School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien Kyuban-cho, Nishinomiya 663-8179, Japan. okada@mwu.mukogawa-u.ac.jp
Semma
Masanori
M
Kitahata
Sumio
S
Ichikawa
Atsushi
A
D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D002851:Chromatography, High Pressure Liquid; D040503:Coffea / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008553:Melibiose / Q000378:metabolism; D012639:Seeds / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D047391:alpha-Cyclodextrins / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D000519:alpha-Galactosidase / Q000378:metabolism
D002247:Carbon Isotopes; D047391:alpha-Cyclodextrins; D008553:Melibiose; D000519:alpha-Galactosidase