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,...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-03, Vol.8 (6), p.1415-1423
Main Authors: Boyd, Derek R, Sharma, Narain D, Bowers, Nigel I, Coen, Gerard B, Malone, John F, O'Dowd, Colin R, Stevenson, Paul J, Allen, Christopher C R
Format: Article
Language:English
Subjects:
Benzoates - chemistry
Benzoates - metabolism
Biocatalysis
Carbasugars - chemical synthesis
Carbasugars - chemistry
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Oxygenases - metabolism
Pseudomonas putida - enzymology
Stereoisomerism
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b921545j