Inactivation of gamma-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-furancarboxylic acid does not proceed by the expected aromatization mechanism

Mengmeng Fu; Richard B Silverman

doi:10.1016/j.bmcl.2003.09.065

Inactivation of gamma-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-furancarboxylic acid does not proceed by the expected aromatization mechanism

Bioorg Med Chem Lett. 2004 Jan 5;14(1):203-6. doi: 10.1016/j.bmcl.2003.09.065.

Authors

Mengmeng Fu¹, Richard B Silverman

Affiliation

¹ Department of Chemistry, Northwestern University, Evanston, IL 60208-3113, USA.

PMID: 14684328
DOI: 10.1016/j.bmcl.2003.09.065

Abstract

Inactivation of pyridoxal 5'-phosphate (PLP)-dependent gamma-aminobutryic acid aminotransferase by (S)-4-amino-4,5-dihydro-2-furancarboxylic acid (SADFA) gives pyridoxamine 5'-phosphate, not the expected SADFA-PLP aromatization product. Inactivation appears to proceed by a Michael addition/hydrolysis mechanism instead.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

4-Aminobutyrate Transaminase / antagonists & inhibitors*
4-Aminobutyrate Transaminase / metabolism*
Carboxylic Acids / chemistry*
Carboxylic Acids / metabolism*
Carboxylic Acids / pharmacology
Dose-Response Relationship, Drug

Substances

Carboxylic Acids
4-Aminobutyrate Transaminase

Grants and funding

NS 15703/NS/NINDS NIH HHS/United States