Synthesis of novel heterobranched beta-cyclodextrins having beta-D-N-acetylglucosaminyl-maltotriose on the side chain.
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.
Tanimoto
Toshiko
T
School of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya 663-8179, Japan. tanimoto@mwu.mukogawa-u.ac.jp
Omatsu
Mizue
M
Ikuta
Akiko
A
Nishi
Yuki
Y
Murakami
Hiromi
H
Nakano
Hirofumi
H
Kitahata
Sumio
S
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*
D014312:Trisaccharides; D047392:beta-Cyclodextrins; C503521:beta-D-N-acetylglucosaminyl-maltotriose; D005944:Glucosamine