Canavanine

Canavanine is a non-proteinogenic amino acid found in certain leguminous plants. Structurally analogous to L-arginine, it differs by the replacement of a methylene group with an oxygen atom. Canavanine acts as a potent antimetabolite of arginine and is mistakenly incorporated into proteins in place of arginine by many organisms. This incorporation leads to the production of structurally aberrant and dysfunctional proteins that disrupt essential biochemical processes such as RNA and DNA metabolism and protein synthesis[3][6]. Canavanine also inhibits enzymes that utilize L-arginine—including nitric oxide synthase isoforms (notably inducible nitric oxide synthase/iNOS)[1][5]—and interferes with arginine uptake and metabolism[4][6]. In plants, it serves as a defensive allelochemical against herbivores due to its toxicity when consumed[3][8]. Experimentally, canavanine has demonstrated antitumor activity in preclinical models but has not been developed or approved for pharmaceutical use[7]. It is considered toxic at certain doses and may induce autoimmune-like symptoms in mammals.

Other names

L-canavanine(L)-canavanine2-amino-4-(guanidinooxy)butyric acidO-((aminoiminomethyl)amino)-L-homoserinecanavanin