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Title: Reaction of phosphoenolpyruvate carboxylase with (Z)-3-bromophosphoenolpyruvate and (Z)-3-fluorophosphoenolpyruvate

Abstract

(Z)-3-Bromophosphoenolpyruvate inactivates phosphoenolpyruvate carboxylase from maize in the presence of HCO/sub 3//sup -/ and either Mg/sup 2 +/ or Mn/sup 2 +/. The inactivation rate follows saturation kinetics. Inactivation is slower in the presence of phospholactate or epoxymaleate, both of which are inhibitors of the enzyme, or dithiothreitol. Inactivation is completely prevented by the presence of lactate dehydrogenase and NADH, and 3-bromolactate is formed during this treatment. If the reaction is conducted by using HC/sup 18/O/sub 3//sup -/, the inorganic phosphate produced contains /sup 18/O. This and other evidence indicate that phosphoenolpyruvate carboxylase catalyzes conversion of bromophosphoenolpyruvate into bromopyruvate by way of the usual carboxyphosphate-enolate intermediate, and bromopyruvate is the species responsible for enzyme inactivation. (Z)-3-fluorophosphoenolpyruvate is transformed by the enzyme into a 6:1 mixture of 3-fluoropyruvate and 3-fluorooxalacetate, presumably by the same mechanism. The enzyme is not inactivated during this treatment.

Authors:
; ;
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison (USA)
OSTI Identifier:
5272344
Resource Type:
Journal Article
Journal Name:
Biochemistry; (United States)
Additional Journal Information:
Journal Volume: 27:4
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 62 RADIOLOGY AND NUCLEAR MEDICINE; CARBOXY-LYASES; BIOCHEMICAL REACTION KINETICS; MASS SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; LABELLED COMPOUNDS; PYRUVIC ACID; BIOCHEMISTRY; BROMINE 79; BROMINE 81; INACTIVATION; MAIZE; MASS SPECTROMETERS; ORGANIC BROMINE COMPOUNDS; OXYGEN 18; PHOSPHORUS 31; BROMINE ISOTOPES; CARBON-CARBON LYASES; CARBOXYLIC ACIDS; CEREALS; CHEMISTRY; ENZYMES; EVEN-EVEN NUCLEI; GRASS; INTERMEDIATE MASS NUCLEI; ISOTOPES; KETO ACIDS; KINETICS; LIGHT NUCLEI; LYASES; MAGNETIC RESONANCE; MEASURING INSTRUMENTS; NUCLEI; ODD-EVEN NUCLEI; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; OXYGEN ISOTOPES; PHOSPHORUS ISOTOPES; PLANTS; RADIOISOTOPES; REACTION KINETICS; RESONANCE; SECONDS LIVING RADIOISOTOPES; SPECTROMETERS; SPECTROSCOPY; STABLE ISOTOPES; 550201* - Biochemistry- Tracer Techniques; 550601 - Medicine- Unsealed Radionuclides in Diagnostics

Citation Formats

Diaz, E, O'Laughlin, J T, and O'Leary, M H. Reaction of phosphoenolpyruvate carboxylase with (Z)-3-bromophosphoenolpyruvate and (Z)-3-fluorophosphoenolpyruvate. United States: N. p., 1988. Web. doi:10.1021/bi00404a037.
Diaz, E, O'Laughlin, J T, & O'Leary, M H. Reaction of phosphoenolpyruvate carboxylase with (Z)-3-bromophosphoenolpyruvate and (Z)-3-fluorophosphoenolpyruvate. United States. https://doi.org/10.1021/bi00404a037
Diaz, E, O'Laughlin, J T, and O'Leary, M H. Tue . "Reaction of phosphoenolpyruvate carboxylase with (Z)-3-bromophosphoenolpyruvate and (Z)-3-fluorophosphoenolpyruvate". United States. https://doi.org/10.1021/bi00404a037.
@article{osti_5272344,
title = {Reaction of phosphoenolpyruvate carboxylase with (Z)-3-bromophosphoenolpyruvate and (Z)-3-fluorophosphoenolpyruvate},
author = {Diaz, E and O'Laughlin, J T and O'Leary, M H},
abstractNote = {(Z)-3-Bromophosphoenolpyruvate inactivates phosphoenolpyruvate carboxylase from maize in the presence of HCO/sub 3//sup -/ and either Mg/sup 2 +/ or Mn/sup 2 +/. The inactivation rate follows saturation kinetics. Inactivation is slower in the presence of phospholactate or epoxymaleate, both of which are inhibitors of the enzyme, or dithiothreitol. Inactivation is completely prevented by the presence of lactate dehydrogenase and NADH, and 3-bromolactate is formed during this treatment. If the reaction is conducted by using HC/sup 18/O/sub 3//sup -/, the inorganic phosphate produced contains /sup 18/O. This and other evidence indicate that phosphoenolpyruvate carboxylase catalyzes conversion of bromophosphoenolpyruvate into bromopyruvate by way of the usual carboxyphosphate-enolate intermediate, and bromopyruvate is the species responsible for enzyme inactivation. (Z)-3-fluorophosphoenolpyruvate is transformed by the enzyme into a 6:1 mixture of 3-fluoropyruvate and 3-fluorooxalacetate, presumably by the same mechanism. The enzyme is not inactivated during this treatment.},
doi = {10.1021/bi00404a037},
url = {https://www.osti.gov/biblio/5272344}, journal = {Biochemistry; (United States)},
number = ,
volume = 27:4,
place = {United States},
year = {1988},
month = {2}
}