Canavanine

Structural formula
General
Surname	Canavanine
other names	L -α-amino-γ- (guanidinooxy) - n -butyric acid O - [(Aminoimminomethyl) amino] homoserine 2-amino-4- (guanidinooxy) butyric acid
Molecular formula	C 5 H 12 N 4 O 3
External identifiers / databases
CAS number 543-38-4 EC number 624-714-2 ECHA InfoCard 100.153.281 PubChem 439202 ChemSpider 388342 DrugBank DB01833 Wikidata Q418408
properties
Molar mass	176.18 g mol −1
Physical state	firmly
Melting point	184 ° C 172 ° C (sulfate, decomposition)
solubility	soluble in water: <100 g · l −1
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302-312-332 P: 280
Toxicological data	5900 mg kg −1 ( LD 50 ,  rat ,  sc )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Canavanine is a non- canonical , non-proteinogenic amino acid that is harmful to health and is found in the seeds of legumes as protection against feeding. The poisonous effect of canavanine is based on the competition between canavanine and the essential amino acid arginine . Since the enzymes of the organism cannot differentiate between the two amino acids, the wrong amino acid is incorporated into the resulting amino acid chains (unfolded proteins). Correct folding then cannot take place, which leads to the failure of protein function.

Individual evidence

1. ↑ ^{a b} entry on canavanine. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
2. ↑ ^{a b c d} L-Canavanine data sheet from Sigma-Aldrich , accessed on March 15, 2011 ( PDF ).