Document Detail


Thiazolidine-2-carboxylic acid, an adduct of cysteamine and glyoxylate, as a substrate for D-amino acid oxidase.
MedLine Citation:
PMID:  6120164     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A mixture of cysteamine and glyoxylate, proposed by Hamilton et al. to form the physiological substrate of hog kidney D-amino acid oxidase (Hamilton, G. A., Buckthal, D. J., Mortensen, R. M., and Zerby, K. W. (1979) Proc. Natl. Acad. Sci. U. S. A. 76, 2625-2629), was confirmed to act as a good substrate for the pure enzyme. As proposed by those workers, it was shown that the actual substrate is thiazolidine-2-carboxylic acid, formed from cysteamine and glyoxylate with a second order rate constant of 84 min-1 M-1 at 37 degrees C, pH 7.5. Steady state kinetic analyses reveal that thiazolidine-2-carboxylic acid is a better substrate at pH 8.5 than at pH 7.5. At both pH values, the catalytic turnover number is similar to that obtained with D-proline. D-Amino acid oxidase is rapidly reduced by thiazolidine-2-carboxylic acid to form a reduced enzyme-imino acid complex, as is typical with D-amino acid oxidase substrates. The product of oxidation was shown by NMR to be delta 2-thiazoline-2-carboxylic acid. Racemic thiazolidine-2-carboxylic acid is completely oxidized by the enzyme. The directly measured rate of isomerization of L-thiazolidine-2-carboxylic acid to the D-isomer was compared to the rate of oxidation of the L-isomer by D-amino acid oxidase. Their identity over the range of temperature from 2-30 degrees C established that the apparent activity with the L-amino acid can be explained quantitatively by the rapid, prior isomerization to D-thiazolidine-2-carboxylic acid.
Authors:
P F Fitzpatrick; V Massey
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  257     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1982 Feb 
Date Detail:
Created Date:  1982-04-20     Completed Date:  1982-04-20     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1166-71     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Amino Acids, Sulfur
Animals
Cysteamine
D-Amino-Acid Oxidase / metabolism*
Glyoxylates
Kidney / enzymology
Kinetics
Proline / analogs & derivatives*
Substrate Specificity
Swine
Thiazolidines
Grant Support
ID/Acronym/Agency:
GM 11106/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Amino Acids, Sulfur; 0/Glyoxylates; 0/Thiazolidines; 147-85-3/Proline; 16310-13-7/thiazolidine-2-carboxylic acid; 298-12-4/glyoxylic acid; 60-23-1/Cysteamine; EC 1.4.3.3/D-Amino-Acid Oxidase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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