L-Canavanine
L-Canavanine Basic information
- Product Name:
- L-Canavanine
- Synonyms:
-
- 2-amino-4-(guanidinooxy)butyricacid
- canavanin
- canavanine
- o-((aminoiminomethyl)amino)-l-homoserin
- o-((aminoiminomethyl)amino)-l-homoserine
- o-[(aminoiminomethyl)amino]homoserine
- L-CANAVANINE
- L-ALPHA-AMINO-GAMMA-[GUANIDINOOXY]-N-BUTYRIC ACID
- CAS:
- 543-38-4
- MF:
- C5H12N4O3
- MW:
- 176.17
- Mol File:
- 543-38-4.mol
L-Canavanine Chemical Properties
- Melting point:
- 184°
- alpha
- D20 +7.9° (c = 3.2)
- Boiling point:
- 307.78°C (rough estimate)
- Density
- 1.3685 (rough estimate)
- refractive index
- 1.7900 (estimate)
- storage temp.
- 2-8°C
- solubility
- H2O: <100 mg/mL
- form
- powder
- pka
- pK1: 2.50(+2);pK2: 6.60(+1);pK3: 9.25(0) (25°C)
Safety Information
- Hazard Codes
- Xn
- Risk Statements
- 20/21/22
- Safety Statements
- 36
- WGK Germany
- 3
- RTECS
- ES7002000
- Hazardous Substances Data
- 543-38-4(Hazardous Substances Data)
MSDS
- Language:English Provider:SigmaAldrich
L-Canavanine Usage And Synthesis
Uses
NO synthase inhibitor
Definition
ChEBI: A non-proteinogenicL-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinoge ic.
Biochem/physiol Actions
Canavanine is a naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). Overproduction of NO by iNOS plays a crucial role in the pathophysiology of septic shock and chronic inflammation.
Purification Methods
Crystallise S-canavanine from absolute EtOH or aqueous EtOH. [Tomiyama J Biol Chem 111 48 1935 gave pK9.25 (COOH), pK 7.4 (guanidinium), pK 11.5 (NH4+), Gulland & Morris J Chem Soc 763 1935,(±) Frankel et al. J Chem Soc 3127 1963, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2622-2628 1961, Beilstein 4 III 1636, 4 IV 3188.]
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