title: Galactosyl transfer ability of beta-(1-->4)-galactosyltransferase toward 5a-carba-sugars.
abstract: Bovine beta-(1-->4)-galactosyltransferase was assayed with a series of 5a-carba-sugars, i.e., sugar analogues in which the ring oxygen of pyranose is replaced by a methylene group. The analogues are 5a-carba-sugar of 2-acetamido-2-deoxy-alpha-DL-galactopyranose, both alpha and beta anomers of 2-acetamido-2-deoxy-DL-glucopyranose (5a-carba-DL-GlcNAc), and 2-acetamido-2-deoxy-DL-mannopyranose. Of these analogues, both alpha and beta anomers of 5a-carba-DL-GlcNAc act as an acceptor. Enzymatic synthesis using the alpha and beta anomers of 5a-carba-DL-GlcNAc afforded the corresponding D-Gal-beta-(1-->4)-5a-carba-alpha-D-GlcNAc and D-Gal-beta-(1-->4)-5a-carba-beta-D-GlcNAc on a practical scale, and these structures were confirmed by NMR spectroscopy. These results indicate that the ring oxygen atom in the 5a-carba-D-GlcNAc is not used for specific recognition by bovine beta-(1-->4)-galactosyltransferase.
authors.affiliation: Department of System Function, Faculty of Science, Yokohama City University, Japan. kajihara@yokohama-cu.ac.jp
authors.forename: Y
authors.initials: Y
authors.lastname: Kajihara
authors.forename: H
authors.initials: H
authors.lastname: Hashimoto
authors.forename: S
authors.initials: S
authors.lastname: Ogawa
mesh_terms: D000818:Animals; D002417:Cattle; D005690:Galactose / Q000737:chemistry / Q000378:metabolism; D005947:Glucose / Q000737:chemistry / Q000378:metabolism; D006838:Hydrocarbons; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D009237:N-Acetyllactosamine Synthase / Q000737:chemistry / Q000378:metabolism*; D010100:Oxygen / Q000737:chemistry; D013379:Substrate Specificity
chemical_list: D006838:Hydrocarbons; C030011:carbene; D009237:N-Acetyllactosamine Synthase; D005947:Glucose; D008697:Methane; D010100:Oxygen; D005690:Galactose