Chemoenzymatic synthesis of the carbasugars carba-beta-L-galactopyranose, carba-beta-L-talopyranose and carba-alpha-L-talopyranose from methyl benzoate

Derek R Boyd; Narain D Sharma; Nigel I Bowers; Gerard B Coen; John F Malone; Colin R O'Dowd; Paul J Stevenson; Christopher C R Allen

doi:10.1039/b921545j

Chemoenzymatic synthesis of the carbasugars carba-beta-L-galactopyranose, carba-beta-L-talopyranose and carba-alpha-L-talopyranose from methyl benzoate

Org Biomol Chem. 2010 Mar 21;8(6):1415-23. doi: 10.1039/b921545j. Epub 2010 Jan 21.

Authors

Derek R Boyd¹, Narain D Sharma, Nigel I Bowers, Gerard B Coen, John F Malone, Colin R O'Dowd, Paul J Stevenson, Christopher C R Allen

Affiliation

¹ School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk

PMID: 20204216
DOI: 10.1039/b921545j

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzoates / chemistry*
Benzoates / metabolism*
Biocatalysis
Carbasugars / chemical synthesis*
Carbasugars / chemistry*
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Oxygenases / metabolism*
Pseudomonas putida / enzymology
Stereoisomerism

Substances

Benzoates
Carbasugars
methyl benzoate
Oxygenases
toluene dioxygenase