title: Chemoenzymatic synthesis of the carbasugars carba-beta-L-galactopyranose, carba-beta-L-talopyranose and carba-alpha-L-talopyranose from methyl benzoate.
abstract: The cis-dihydrodiol metabolite from methyl benzoate has been used as a synthetic precursor of carba-beta-L-galactopyranose, carba-beta-L-talopyranose and carba-alpha-L-talopyranose. The structures and absolute configurations of these carbasugars were determined by a combination of NMR spectroscopy, stereochemical correlation and X-ray crystallography.
authors.affiliation: School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
authors.forename: Derek R
authors.initials: DR
authors.lastname: Boyd
authors.forename: Narain D
authors.initials: ND
authors.lastname: Sharma
authors.forename: Nigel I
authors.initials: NI
authors.lastname: Bowers
authors.forename: Gerard B
authors.initials: GB
authors.lastname: Coen
authors.forename: John F
authors.initials: JF
authors.lastname: Malone
authors.forename: Colin R
authors.initials: CR
authors.lastname: O'Dowd
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Stevenson
authors.forename: Christopher C R
authors.initials: CC
authors.lastname: Allen
mesh_terms: D001565:Benzoates / Q000737:chemistry* / Q000378:metabolism*; D055162:Biocatalysis; D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D010105:Oxygenases / Q000378:metabolism*; D016958:Pseudomonas putida / Q000201:enzymology; D013237:Stereoisomerism
chemical_list: D001565:Benzoates; D054329:Carbasugars; C044605:methyl benzoate; D010105:Oxygenases; C023172:toluene dioxygenase