PMID: 6990987Jan 1, 1980Paper

Phosphonate analogues of pyruvate. Probes of substrate binding to pyruvate oxidase and other thiamin pyrophosphate-dependent decarboxylases

Biochimica Et Biophysica Acta
T A O'BrienR B Gennis

Abstract

A number of enzymes catalyze the removal of carbon dioxide from pyruvate through covalent participation of the coenzyme thiamin pyrophosphate. The conversions of the decarboxylated adduct, hydroxyethyl thiamin pyrophosphate, to subsequent products distinguishes the function of these enzymes. Acetaldehyde is produced by pyruvate decarboxylase, acetic acid by pyruvate oxidase and acetyl coenzyme A by pyruvate dehydrogenase. Differences and details of steps prior to decomposition of hydroxyethyl thiamin pyrophosphate can be evaluated through the use of two substrate analogues, methyl acetylphosphonate and acetylphosphonate. Methyl acetylphosphonate and acetylphosphonate are competitive inhibitors toward pyruvate with Escherichia coli pyruvate oxidase and E. coli pyruvate dehydrogenase but the value of the Ki for the oxidase is more than three orders of magnitude higher than for the dehydrogenase. Yeast pyruvate decarboxylase is not inhibited at all under the same conditions. The binding of methyl acetylphosphonate results in ligand-induced changes in the near ultraviolet circular dichorism spectrum of the oxidase. This spectral perturbation is only seen in the presence of the cofactor, thiamin pyrophosphate, strongly suggesting th...Continue Reading

References

Mar 30, 1978·Biochemical and Biophysical Research Communications·L S Leung, P A Frey
Sep 26, 1966·Archives of Biochemistry and Biophysics·F R Williams, L P Hager

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Citations

Sep 28, 2010·Chemical Communications : Chem Comm·Michael Kuemin, Wilfred A van der Donk
Sep 30, 2010·Proceedings of the National Academy of Sciences of the United States of America·Jin-Hee LeeWilfred A van der Donk
Jun 19, 2013·Proceedings of the National Academy of Sciences of the United States of America·Despina J BougioukouWilfred A van der Donk
Sep 1, 2011·The Journal of Biological Chemistry·Leighanne A BrammerCaren Freel Meyers
May 4, 2011·Antimicrobial Agents and Chemotherapy·Benjamin T CircelloWilliam W Metcalf
Oct 31, 2013·The Journal of Antibiotics·Jessica M SmithCaren L Freel Meyers
Nov 4, 2015·Accounts of Chemical Research·Ronald Kluger
Apr 27, 2010·Chemistry & Biology·Benjamin T CircelloWilliam W Metcalf
Jan 7, 2017·Chemical Reviews·Mireille MoutiezMuriel Gondry
Oct 28, 2016·Chemical Reviews·Geoff P Horsman, David L Zechel
Jan 26, 1987·FEBS Letters·E W SzczepanT Viswanatha
Jan 12, 2019·Organic & Biomolecular Chemistry·M Mercedes Jiménez-AndreuCarlos Cativiela
Jan 1, 1982·Annals of the New York Academy of Sciences·R Kluger
Jul 16, 2015·Chembiochem : a European Journal of Chemical Biology·David BarteeCaren L Freel Meyers
Apr 17, 2020·Microbiology and Molecular Biology Reviews : MMBR·Rachel M Burckhardt, Jorge C Escalante-Semerena
May 22, 2008·Chemical Reviews·Ronald Kluger, Kai Tittmann
Jun 27, 2018·Biochemistry·David Bartee, Caren L Freel Meyers
Mar 21, 2007·Journal of the American Chemical Society·Asim K BeraMiriam S Hasson

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