Isolation and structural analyses of positional isomers of 6(1),6(n)-di-O-(N-acetyl-beta-D-glucosaminyl)cyclomaltoheptaose (n=2, 3, and 4) and 6-O-[6-O-(N-acetyl-beta-D-glucosaminyl)-N-acetyl-beta-D-glucosaminyl]cyclomaltoheptaose.
6-O-[6-O-(N-acetyl-beta-D-glucosaminyl)-N-acetyl-beta-D-glucosaminyl]cyclomaltoheptaose (beta CD) and three positional isomers of 6(1),6(n)-di-O-(N-acetyl-beta-D-glucosaminyl)cyclomaltoheptaose (n=2, 3, and 4) in a mixture of products from beta CD and N-acetylglucosamine by the reversed reaction of beta-N-acetylhexosaminidase from jack bean were isolated and purified by HPLC. The structures of four isomers of di-N-acetylglucosaminyl-beta CDs were determined by FABMS and NMR spectroscopy. The degree of polymerization of the branched oligosaccharides produced by enzymatic degradation with bacterial saccharifying alpha-amylase (BSA) was established by LC-MS methods.
Okada
Y
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
M
M
Ito
Y
Y
Hamayasu
K
K
Fujita
K
K
Hashimoto
H
H
Koizumi
K
K
Kitahata
S
S
D000117:Acetylglucosamine / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D007887:Fabaceae / Q000201:enzymology; D005944:Glucosamine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D025942:Oligosaccharides, Branched-Chain / Q000737:chemistry / Q000302:isolation & purification; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism
D003505:Cyclodextrins; D025942:Oligosaccharides, Branched-Chain; C448924:di-O-(N-acetyl-glucosaminyl)cyclomaltoheptaose; D001619:beta-N-Acetylhexosaminidases; D005944:Glucosamine; D000117:Acetylglucosamine