L-canaline

-Canaline (IUPAC name 2-amino-4-(aminooxy)butyric acid)) is a non-proteinogenic amino acid. The compound is found in legumes that contain canavanine, from which it is produced by the action of arginase. The most common-used source for this amino acid is the jack bean, Canavalia ensiformis.

== Toxicity == -Canaline is the only naturally occurring amino acid known that has an O-alkyl hydroxylamine functionality in the side chain. This amino acid is structurally related to ornithine (it is the 5-oxa derivative) and is a potent insecticide. Tobacco hornworm larvae fed a diet containing 2.5 mM canaline showed massive developmental aberrations, and most larvae so treated died at the pupal stage. It also exhibits potent neurotoxic effects in the moth. thumb|L-Canaline is a substrate for Ornithine aminotransferase Its toxicity stems primarily from the fact that it readily forms oximes with keto acids and aldehydes, especially the pyridoxal phosphate cofactor of many vitamin B6-dependent enzymes. It inhibits ornithine aminotransferase at concentrations as low as 10 nM.