Chemoenzymatic synthesis of the carbasugars carba-beta-L-galactopyranose, carba-beta-L-talopyranose and carba-alpha-L-talopyranose from methyl benzoate.
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.
Boyd
Derek R
DR
School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
Sharma
Narain D
ND
Bowers
Nigel I
NI
Coen
Gerard B
GB
Malone
John F
JF
O'Dowd
Colin R
CR
Stevenson
Paul J
PJ
Allen
Christopher C R
CC
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
D001565:Benzoates; D054329:Carbasugars; C044605:methyl benzoate; D010105:Oxygenases; C023172:toluene dioxygenase