title: Synthesis of novel heterobranched beta-cyclodextrins having beta-D-N-acetylglucosaminyl-maltotriose on the side chain.
abstract: From a mixture of N-acetylglucosaminyl-beta-cyclodextrin (GlcNAc-betaCD) and lactose, beta-D-galactosyl-GlcNAc-betaCD (Gal-GlcNAc-betaCD) was synthesized by the transfer action of beta-galactosidase. GlcNAc-maltotriose (Glc3) and Gal-GlcNAc-Glc3 were produced with hydrolysis of GlcNAc-betaCD by cyclodextrin glycosyltransferase, and Gal-GlcNAc-betaCD by bacterial saccharifying alpha-amylase respectively. Finally, GlcNAc-Glc3-betaCD and Gal-GlcNAc-Glc3-betaCD were synthesized in 5.2% and 3.5% yield when Klebsiella pneumoniae pullulanase was incubated with the mixture of GlcNAc-Glc(3) and betaCD, or Gal-GlcNAc-Glc3 and betaCD respectively. The structures of GlcNAc-Glc3-betaCD and Gal-GlcNAc-Glc3-betaCD were analyzed by FAB-MS and NMR spectroscopy and identified as 6-O-alpha-(6(3)-O-beta-D-N-acetylglucosaminyl-maltotriosyl)-betaCD, and 6-O-alpha-(4-O-beta-D-galactopyranosyl-6(3)-O-beta-D-N-acetylglucosaminyl-maltotriosyl)-betaCD respectively.
authors.affiliation: School of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya 663-8179, Japan. tanimoto@mwu.mukogawa-u.ac.jp
authors.forename: Toshiko
authors.initials: T
authors.lastname: Tanimoto
authors.forename: Mizue
authors.initials: M
authors.lastname: Omatsu
authors.forename: Akiko
authors.initials: A
authors.lastname: Ikuta
authors.forename: Yuki
authors.initials: Y
authors.lastname: Nishi
authors.forename: Hiromi
authors.initials: H
authors.lastname: Murakami
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Nakano
authors.forename: Sumio
authors.initials: S
authors.lastname: Kitahata
mesh_terms: D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014312:Trisaccharides / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D014312:Trisaccharides; D047392:beta-Cyclodextrins; C503521:beta-D-N-acetylglucosaminyl-maltotriose; D005944:Glucosamine