Suicide inhibition of alpha-oxamine synthases: structures of the covalent adducts of 8-amino-7-oxononanoate synthase with trifluoroalanine

Dmitriy Alexeev; Robert L Baxter; Dominic J Campopiano; Olivier Kerbarh; Lindsay Sawyer; Nicholas Tomczyk; Rory Watt; Scott P Webster

doi:10.1039/b517922j

Suicide inhibition of alpha-oxamine synthases: structures of the covalent adducts of 8-amino-7-oxononanoate synthase with trifluoroalanine

Dmitriy Alexeev, Robert L Baxter, Dominic J Campopiano, Olivier Kerbarh, Lindsay Sawyer, Nicholas Tomczyk, Rory Watt, Scott P Webster

Research output: Contribution to journal › Article › peer-review

Abstract

The irreversible inhibition of 8-amino-7-oxononanoate synthase by trifluoroalanine involves decarboxylative defluorination of the inhibitor-PLP aldimine followed by attack of the conjugated imine by the amino group of the active site lysine to afford a covalently bound difluorinated intermediate which can subsequently undergo further HF losses and hydrolysis to afford a 2-(pyridoximine phosphate) acetoyl protein adduct.

Original language	English
Pages (from-to)	1209-12
Number of pages	4
Journal	Organic & Biomolecular chemistry
Volume	4
Issue number	7
DOIs	https://doi.org/10.1039/b517922j
Publication status	Published - 2006

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title = "Suicide inhibition of alpha-oxamine synthases: structures of the covalent adducts of 8-amino-7-oxononanoate synthase with trifluoroalanine",

abstract = "The irreversible inhibition of 8-amino-7-oxononanoate synthase by trifluoroalanine involves decarboxylative defluorination of the inhibitor-PLP aldimine followed by attack of the conjugated imine by the amino group of the active site lysine to afford a covalently bound difluorinated intermediate which can subsequently undergo further HF losses and hydrolysis to afford a 2-(pyridoximine phosphate) acetoyl protein adduct.",

author = "Dmitriy Alexeev and Baxter, \{Robert L\} and Campopiano, \{Dominic J\} and Olivier Kerbarh and Lindsay Sawyer and Nicholas Tomczyk and Rory Watt and Webster, \{Scott P\}",

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doi = "10.1039/b517922j",

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AU - Alexeev, Dmitriy

AU - Baxter, Robert L

AU - Campopiano, Dominic J

AU - Kerbarh, Olivier

AU - Sawyer, Lindsay

AU - Tomczyk, Nicholas

AU - Watt, Rory

AU - Webster, Scott P

PY - 2006

Y1 - 2006

N2 - The irreversible inhibition of 8-amino-7-oxononanoate synthase by trifluoroalanine involves decarboxylative defluorination of the inhibitor-PLP aldimine followed by attack of the conjugated imine by the amino group of the active site lysine to afford a covalently bound difluorinated intermediate which can subsequently undergo further HF losses and hydrolysis to afford a 2-(pyridoximine phosphate) acetoyl protein adduct.

AB - The irreversible inhibition of 8-amino-7-oxononanoate synthase by trifluoroalanine involves decarboxylative defluorination of the inhibitor-PLP aldimine followed by attack of the conjugated imine by the amino group of the active site lysine to afford a covalently bound difluorinated intermediate which can subsequently undergo further HF losses and hydrolysis to afford a 2-(pyridoximine phosphate) acetoyl protein adduct.

U2 - 10.1039/b517922j

DO - 10.1039/b517922j

M3 - Article

C2 - 16557306

SN - 1477-0520

VL - 4

SP - 1209

EP - 1212

JO - Organic & Biomolecular chemistry

JF - Organic & Biomolecular chemistry

IS - 7

ER -

Suicide inhibition of alpha-oxamine synthases: structures of the covalent adducts of 8-amino-7-oxononanoate synthase with trifluoroalanine

Abstract

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