C9758

L-Canavanine sulfate salt

≥99% (TLC), powder

• Synonym(s): L-α-Amino-γ-(guanidinooxy)butyric acid sulfate salt
• Empirical Formula (Hill Notation): C₅H₁₂N₄O₃ · H₂SO₄
• CAS Number: 2219-31-0
• Molecular Weight: 274.25
• Beilstein: 6121291
• EC Number: 218-728-4
• MDL number: MFCD00012618
• UNSPSC Code: 12352209
• PubChem Substance ID: 24278349
• NACRES: NA.32

Properties

• biological source: plant seeds (Jack bean )
• Assay: ≥99% (TLC)
• form: powder
• color: white
• mp: 160-165 °C (dec.)
• solubility: H₂O: 100 mg/mL
• storage temp.: 2-8°C
• SMILES string: OS(O)(=O)=O.N[C@@H](CCONC(N)=N)C(O)=O
• InChI: 1S/C5H12N4O3.H2O4S/c6-3(4(10)11)1-2-12-9-5(7)8;1-5(2,3)4/h3H,1-2,6H2,(H,10,11)(H4,7,8,9);(H2,1,2,3,4)/t3-;/m0./s1
• InChI key: MVIPJKVMOKFIEV-DFWYDOINSA-N
• Gene Information: human ... NOS2(4843)

Description

General description

Canavanine is a homolog of arginine and a non-protein amino acid. It is present in plants like alfalfa, cloves, beans onions and sprouts. Canavanine is synthesized from L-canavaninosuccinic acid and the biosynthetic pathway was first elucidated in jack bean plant.

Application

Canavanine sulfate salt has been used:

• as a translation inhibitor in yeast translation studies
• as a component of synthetic complete (SC) drop-out medium for screening yeast
• for screening Saccharomyces cerevisiae in canavanine mutation frequency assay

Biochem/physiol Actions

Canavanine is a naturally occurring L-amino acid that competes and interferes with L-arginine-utilizing enzymes due to its structural similarity with this L-amino acid. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). It acts as a substrate for arginyl tRNA and is incorporated during protein synthesis leading to aberrant canavanyl proteins. Supplementation with canavanine worsens the alfalfa induced Systemic lupus erythematosus (SLE) like syndrome and its incorporation with endosome and proteasome disrupts the antigen processing.

Naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity with this L-amino acid. It is a selective inhibitor of inducible nitric oxide synthase (iNOS).

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves