Metabolic solutions to the biosynthesis of some diaminomonocarboxylic acids in nature: Formation in cyanobacteria of the neurotoxins 3-N-methyl-2,3-diaminopropanoic acid (BMAA) and 2,4-diaminobutanoic acid (2,4-DAB)

Citation

Nunn PB & Codd G (2017) Metabolic solutions to the biosynthesis of some diaminomonocarboxylic acids in nature: Formation in cyanobacteria of the neurotoxins 3-N-methyl-2,3-diaminopropanoic acid (BMAA) and 2,4-diaminobutanoic acid (2,4-DAB). Phytochemistry, 144, pp. 253-270. https://doi.org/10.1016/j.phytochem.2017.09.015

Abstract
The non-encoded diaminomonocarboxylic acids, 3-N-methyl-2,3-diaminopropanoic acid (syn: α-amino-β-methylaminopropionic acid, MeDAP; β-N-methylaminoalanine, BMAA) and 2,4-diaminobutanoic acid (2,4-DAB), are distributed widely in cyanobacterial species in free and bound forms. Both amino acids are neurotoxic in whole animal and cell-based bioassays. The biosynthetic pathway to 2,4-DAB is well documented in bacteria and in one higher plant species, but has not been confirmed in cyanobacteria. The biosynthetic pathway to BMAA is unknown. This review considers possible metabolic routes, by analogy with reactions used in other species, by which these amino acids might be biosynthesised by cyanobacteria, which are a widespread potential environmental source of these neurotoxins. Where possible, the gene expression that might be implicated in these biosyntheses is discussed.

Keywords
2,3-Diaminopropanoic acid; 2,3-DAP; 3-N-Methyl-2,3-diaminopropanoic acid; BMAA; 2,4-Diaminobutanoic acid; 2,4-DAB; 2,3-Diaminobutanoic acid; 2,3-DAB; 3-N-Methyl-2,3-diaminobutanoic acid; AMBA; Biosynthesis; Cyanobacteria

Journal
Phytochemistry: Volume 144