canavanine
Sign in to saveAlso known as L-2-Amino-4-(Guanidinooxy)Butyric Acid
L-(+)-(S)-Canavanine is a non-proteinogenic amino acid found in certain leguminous plants. It is structurally related to the proteinogenic α-amino acid L-arginine, the sole difference being the replacement of a methylene bridge ( unit) in arginine with an oxa group (i.e., an oxygen atom) in canavanine. Canavanine is accumulated primarily in the seeds of the organisms which produce it, where it serves both as a highly deleterious defensive compound against herbivores (due to cells mistaking it for arginine) and a vital source of nitrogen for the growing embryo. The related L-canaline is similar
Research
1,092 papersvia PubMed
Wikidata facts
- Mass
- 176.091
Show 4 more facts
- chemical formula
- C₅H₁₂N₄O₃
- canonical SMILES
- C(CON=C(N)N)C(C(=O)O)N
- isomeric SMILES
- C(CON=C(N)N)[C@@H](C(=O)O)N
- Commons category
- Canavanine
via Wikidata · CC0
~5 min read
Article
8 sectionsContents
- Toxicity
- In mammals
- Tolerance
- By metabolic detoxification
- By selectivity
- See also
- References
- Bibliography
{{Chembox | ImageFile = L-S-Canavanine.svg | ImageName = Chemical structure of L-(+)-(S)-canavanine | PIN = Canavanine | SystematicName = (2S)-2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid |Section1= |Section2= |Section3= }}
L-(+)-(S)-Canavanine is a non-proteinogenic amino acid found in certain leguminous plants. It is structurally related to the proteinogenic α-amino acid L-arginine, the sole difference being the replacement of a methylene bridge ( unit) in arginine with an oxa group (i.e., an oxygen atom) in canavanine. Canavanine is accumulated primarily in the seeds of the organisms which produce it, where it serves both as a highly deleterious defensive compound against herbivores (due to cells mistaking it for arginine) and a vital source of nitrogen for the growing embryo. The related L-canaline is similar to ornithine.