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Synthesis and optical resolution of the neurotoxin 2-amino-3-([15N]-methylamino)propanoic acid (BMAA)

✍ Scribed by Yulin Hu; Herman Ziffer

Publisher: John Wiley and Sons
Year: 1990
Tongue: French
Weight: 208 KB
Volume: 28
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580280508

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✦ Synopsis

Abstract

The synthesis of 2‐amino‐3‐([^15^N]‐methylamino)propanoic acid (synonyms, BMAA, β‐N‐methylamino‐alanine) from α‐acetamidoacrylic acid and [^15^N]‐methylamine is described. Enantioselective hydrolysis of the acetamide group, mediated by the enzyme Acylase 1 (EC 3.5.1.14), yielded (R)‐BMAA and the (S)‐α‐acetamido derivative. Acid hydrolysis of the latter compound yielded (S)‐BMAA.

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