Document Detail

Enzymatic reaction of beta-N-methylaminoalanine with L-amino acid oxidase.
MedLine Citation:
PMID:  2043677     Owner:  NLM     Status:  MEDLINE    
The reaction of beta-N-methylaminoalanine (BMAA) with L-amino acid oxidase (L-AAO) in the presence of catalase yields ammonia and beta-N-methylaminopyruvate, which was trapped as its 2,4-dinitrophenylhydrazone, as products. Incubation of BMAA with L-AAO in the presence of semicarbazide led to the formation of a semicarbazone, indicating intermediate iminium ion formation; when potassium cyanide (5 mM) was added, semicarbazone formation was blocked. The formation of beta-N-methylaminopyruvate was decreased by omission of catalase and was reduced in the presence of hydrogen peroxide (100 mM). These results indicate that BMAA is converted by L-AAO to the corresponding alpha-imino acid, which undergoes hydrolysis to beta-N-methylaminopyruvate. The alpha-keto acid is readily oxidized to N-methylglycine by hydrogen peroxide.
M Hashmi; M W Anders
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Biochimica et biophysica acta     Volume:  1074     ISSN:  0006-3002     ISO Abbreviation:  Biochim. Biophys. Acta     Publication Date:  1991 May 
Date Detail:
Created Date:  1991-07-17     Completed Date:  1991-07-17     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0217513     Medline TA:  Biochim Biophys Acta     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  36-9     Citation Subset:  IM    
Department of Pharmacology, University of Rochester, School of Medicine and Dentistry, NY 14642.
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MeSH Terms
Amino Acid Oxidoreductases / chemistry*
Amino Acids, Diamino / chemistry*
Carcinogens / chemistry
Catalase / chemistry
L-Amino Acid Oxidase
Molecular Structure
Potassium Cyanide / chemistry
Semicarbazides / chemistry
Grant Support
Reg. No./Substance:
0/Amino Acids, Diamino; 0/Carcinogens; 0/Semicarbazides; 151-50-8/Potassium Cyanide; 16676-91-8/alpha-amino-beta-methylaminopropionate; 57-56-7/carbamylhydrazine; EC; EC 1.4.-/Amino Acid Oxidoreductases; EC Acid Oxidase

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