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Mechanism of α-oxoamine synthases: identification of the intermediate Claisen product in the 8-amino-7-oxononanoate synthase reaction†
Olivier Kerbarh,Dominic J. Campopiano,Robert L. Baxter
Chemical Communications Pub Date : 11/14/2005 00:00:00 , DOI:10.1039/B511837A
Abstract

The reactive β-ketoacid pyridoxal-5′-phosphate aldimine formed in the condensation step of the 8-amino-7-oxononanoate synthase reaction was ‘trapped’ in the enzyme-bound form by carrying out the reaction with L-alanine methyl ester and pimeloyl-CoA affording the more stable methyl ester of the putative intermediate, the characterisation of which provides the first definitive evidence for a β-ketoacid intermediate in an α-oxamine synthase mechanism.

Graphical abstract: Mechanism of α-oxoamine synthases: identification of the intermediate Claisen product in the 8-amino-7-oxononanoate synthase reaction
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