Inhibition of escherichia coli glucosamine synthetase by novel electrophilic analogues of glutamine—comparison with 6-diazo-5-oxo-norleucine

…, MF Brown, JF Lynas, SL Martin, A McDowell…

Index: Walker, Brian; Brown, Martin F.; Lynas, John F.; Martin; McDowell, Andrew; Badet, Bernard; Hill, Alan J. Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 24 p. 2795 - 2798

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Citation Number: 10

Abstract

A series of electrophilic glutamine analogues based on 6-diazo-5-oxo-norleucine has been prepared, using novel synthetic routes, and evaluated as inhibitors of Escherichia coli. glucosamine synthetase. The γ-dimethylsulphonium salt analogue of glutamine was found to be one of the most potent inactivators of this enzyme yet reported, with an apparent second order rate constant (k2/Ki) of 3.5× 105M− 1 min− 1.