Enzymatic reaction of β-N-methylaminoalanine with l-amino acid oxidase

Add time:09/06/2019    Source:sciencedirect.com

The reaction of β-N-methylaminoalanine (BMAA) with l-amino acid oxidase (l-AAO) in the presence of catalase yields ammonia and β-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 β-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 α-imino acid, which undergoes hydrolysis to β-N-methylaminopyruvate. The α-keto acid is readily oxidized to N-methyllycine by hydrogen peroxide.

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