Work

Stereochemistry of the kynureninase reaction.

Year: 1985

Type: article

Abstract: The steric course of the replacement of the anthranilyl group of kynurenine by hydrogen was determined by conversion of (2S,3R)- and (2S,3S)-[3-3H]kynurenine into alanine with kynureninase in D2O, followed by chirality analysis of the alanine methyl group. To minimize enolization, the labeled substrates were generated in situ from the corresponding stereospecifically tritiated tryptophan species. The result, replacement in a retention mode, together with the finding that tritium from the alpha-position of the substrate is recycled and appears both at C alpha and C beta of the product suggests a single base mechanism and an active site geometry of the pyridoxal phosphate-substrate complex in which H alpha and the beta-substituent are syn oriented.

Source: Journal of Biological Chemistry

DOI: 10.1016/s0021-9258(18)89013-5

Authors: M M Palcic, M Antoun, K Tanizawa, K Soda, H G Floss

Institutions: Purdue University West Lafayette, Kyoto University, The Ohio State University

Language: English

Topic: Chemical Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,430

Funder: National Institute of General Medical Sciences