title: Synthesis of branched cyclomaltooligosaccharide carboxylic acids (cyclodextrin carboxylic acids) by microbial oxidation.
abstract: Novel branched cyclomaltooligosaccharide carboxylic acid (cyclodextrin carboxylic acid) derivatives were synthesized by microbial oxidation using Pseudogluconobacter saccharoketogenes to oxidize five types of branched cyclodextrins, including maltosyl beta-cyclodextrin (maltosyl-beta-CyD). For each novel cyclodextrin carboxylic acid derivative synthesized, the hydroxymethyl group of the terminal glucose residue in the branched part of the molecule was regiospecifically oxidized to a carboxyl group to give the corresponding uronic acid. In addition, the physicochemical properties of cyclomaltoheptaosyl-(6-->1)-alpha-D-glucopyranosyl-(4-->1)-alpha-D-glucopyranosiduronic acid (GUG-beta-CyD) (1) and its sodium salt were studied more extensively, as these compounds are most likely to have a practical application.
authors.affiliation: Biotechnology Department, Pharmaceutical Research Division, Takeda Chemical Industries Ltd., Osaka, Japan. icb54968@nifty.com
authors.forename: T
authors.initials: T
authors.lastname: Ishiguro
authors.forename: T
authors.initials: T
authors.lastname: Fuse
authors.forename: M
authors.initials: M
authors.lastname: Oka
authors.forename: T
authors.initials: T
authors.lastname: Kurasawa
authors.forename: M
authors.initials: M
authors.lastname: Nakamichi
authors.forename: Y
authors.initials: Y
authors.lastname: Yasumura
authors.forename: M
authors.initials: M
authors.lastname: Tsuda
authors.forename: T
authors.initials: T
authors.lastname: Yamaguchi
authors.forename: I
authors.initials: I
authors.lastname: Nogami
mesh_terms: D000426:Alcohol Dehydrogenase / Q000378:metabolism; D001419:Bacteria / Q000201:enzymology; D002236:Carbohydrate Conformation; D003505:Cyclodextrins / Q000096:biosynthesis* / Q000737:chemistry / Q000378:metabolism; D009844:Oligosaccharides / Q000737:chemistry; D010084:Oxidation-Reduction; D013379:Substrate Specificity; D047392:beta-Cyclodextrins
chemical_list: D003505:Cyclodextrins; D009844:Oligosaccharides; D047392:beta-Cyclodextrins; C438085:cyclomaltoheptaosyl-(6-1)-glucopyranosyl-(4-1)-glucopyranosiduronic acid; C075170:6-O-maltosyl-beta-cyclodextrin; D000426:Alcohol Dehydrogenase