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B6db references: 85045537

type Journal Article
authors Bild, G. S.; Morris, J. C.
title Detection of beta-carbanion formation during kynurenine hydrolysis catalyzed by Pseudomonas marginalis kynureninase
journal Arch Biochem Biophys
ui 85045537
year (1984)
volume 235
number 1
pages 41-7.
keywords Benzaldehydes/metabolism
abstract 2-Amino-4-hydroxy-4-phenylbutyric acid has been shown to be formed during the Pseudomonas marginalis kynureninase-catalyzed hydrolysis of kynurenine in the presence of benzaldehyde and pyridoxal phosphate. The formation of 2-amino-4-hydroxy-4-phenylbutyric acid is the first demonstration, to our knowledge, of the controlled trapping of an amino acid beta-carbanion generated either chemically or enzymatically, and is perhaps the best empirical evidence to date that enzyme mechanisms can proceed through a beta-carbanionic intermediate. The lifetime of the beta-carbanionic alanyl intermediate generated by kynureninase is of sufficient duration to allow reaction with benzaldehyde. Other aromatic, but no aliphatic, aldehydes will undergo electrophilic addition with kynureninase-generated beta-carbanionic alanyl intermediates to form the corresponding amino acid.
last changed 2002/11/12 16:17

B6db references