PMID: 2111163Apr 17, 1990Paper

Glucosamine-6-phosphate synthase from Escherichia coli: determination of the mechanism of inactivation by N3-fumaroyl-L-2,3-diaminopropionic derivatives

Biochemistry
N KucharczykB Badet

Abstract

A mechanistic investigation of the inactivation of Escherichia coli glucosamine-6-phosphate synthase by N3-(4-methoxyfumaroyl)-L-2,3-diaminopropionate (FMDP) was undertaken. On the basis of the known participation of the N-terminal cysteine residue in this process [Chmara et al. (1986) Biochim. Biophys. Acta 870, 357; Badet et al. (1988) Biochemistry 27, 2282], the model reactions between FMDP and L-cysteine and between FMDP and the synthetic decapeptide Cys-Gly-Ile-Val-Gly-Ala-Ile-Ala-Gln-Arg, corresponding to the amino-terminal protein sequence, were studied. The results allowed us to propose a pathway that is in perfect agreement with the biochemical results: enzyme inactivation arose from Michael addition of glutamine binding site cysteine-1 on the fumaroyl double bond at the beta-position of the ester group. Upon denaturation under slightly alkaline conditions, this adduct underwent cyclization to a transient succinimide adduct, which rearranged into the stable 2-substituted 1,4-thiazin-3-one-5-carboxylate involving participation of the cysteine amino group. The tryptic radiolabeled peptides purified from [3H]FMDP-treated enzyme and resistant to Edman degradation coeluted with the products resulting from the model reaction...Continue Reading

References

Jan 1, 1987·Reviews of Infectious Diseases·E Drouhet, B Dupont
Mar 1, 1987·Infection·D A Stevens
Feb 1, 1985·Journal of General Microbiology·H Chmara
Jul 1, 1970·The Biochemical Journal·J E Walker, E P Abraham

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Citations

Jun 5, 2002·Biochimica Et Biophysica Acta·Sławomir Milewski
Nov 30, 2011·Chembiochem : a European Journal of Chemical Biology·Robert JędrzejczakSławomir Milewski
May 29, 2012·Chemistry & Biology·Renier van der WesthuyzenErick Strauss
Feb 19, 2008·Archives of Biochemistry and Biophysics·Philippe DurandMarie-Ange Badet-Denisot
Nov 26, 2010·Critical Reviews in Biotechnology·Ankur GautamRupinder Tewari
Jan 1, 1996·Journal of Enzyme Inhibition·M WojciechowskiE Borowski
Apr 14, 2017·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Josef MayrBernhard K Keppler
Jan 1, 2010·Journal of Natural Products·Jessica DawlatyJon Clardy
Dec 26, 2001·Chemical Reviews·X HeH W Liu Hw

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