title: Preparation and characterization of novel branched beta-cyclodextrins having beta-D-galactose residues on the non-reducing terminal of the side chains and their specific interactions with peanut (Arachis hypogaea) agglutinin.
abstract: Six novel branched beta-cyclodextrins (betaCDs) having beta-D-galactose residues on the non-reducing terminal of the sugar side chains, namely 6(1),6(4)-di-O-(beta-D-galactosyl)-betaCD (10), 6-O-(beta-D-galactosyl)-betaCD (11), 6(1),6(4)-di-O-(beta-lactosyl)-betaCD (14), 6-O-(beta-lactosyl)-betaCD (15), 6(1),6(4)-di-O-(4'-O-beta-D-galactosyl-beta-lactosyl)-betaCD (18), and 6-O-(4'-O-beta-D-galactosyl-beta-lactosyl)-betaCD (19), were chemically synthesized using the trichloroacetimidate method. The reaction products were separated by HPLC on an amino column into dibranched and monobranched betaCDs. Their structures were confirmed by mass spectrometry (MS) and two-dimensional (2D) NMR spectroscopic analysis. To study the length of the sugar side chains attached to the CD ring, which leads to differences in the functions of the branched CDs, interactions of these compounds with peanut (Arachis hypogaea) agglutinin (PNA) were investigated using an optical biosensor and an inhibition assay based on hemagglutination. The results showed that all branched betaCDs interacted with PNA, and the binding affinity was 18>14>10 and 19>15>11 when the derivatives were compared on the basis of side chain length.
authors.affiliation: School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien Kyuban-cho, Nishinomiya 663-8179, Japan.
authors.forename: Akiko
authors.initials: A
authors.lastname: Ikuta
authors.forename: Naomi
authors.initials: N
authors.lastname: Mizuta
authors.forename: Sumio
authors.initials: S
authors.lastname: Kitahata
authors.forename: Takeomi
authors.initials: T
authors.lastname: Murata
authors.forename: Taichi
authors.initials: T
authors.lastname: Usui
authors.forename: Kyoko
authors.initials: K
authors.lastname: Koizumi
authors.forename: Toshiko
authors.initials: T
authors.lastname: Tanimoto
mesh_terms: D015374:Biosensing Techniques; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D006385:Hemagglutination Inhibition Tests; D007202:Indicators and Reagents; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D019887:Peanut Agglutinin / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D047392:beta-Cyclodextrins
chemical_list: D003505:Cyclodextrins; D007202:Indicators and Reagents; D019887:Peanut Agglutinin; D047392:beta-Cyclodextrins; C031215:betadex; D005690:Galactose