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C9758 Sigma-Aldrich

L-Canavanine sulfate salt

≥99% (TLC), powder

Synonym: L-α-Amino-γ-(guanidinooxy)butyric acid sulfate salt

  • CAS Number 2219-31-0

  • Empirical Formula (Hill Notation) C5H12N4O3 · H2SO4

  • Molecular Weight 274.25

  •  Beilstein/REAXYS Number 6121291

  •  EC Number 218-728-4

  •  MDL number MFCD00012618

  •  PubChem Substance ID 24278349

  •  NACRES NA.32

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Properties

Related Categories Application Index, Biochemicals and Reagents, Cell Biology, Cell Signaling Enzymes, Cell Signaling and Neuroscience,
Quality Level   200
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

Packaging

1, 5 g in poly bottle

100, 250 mg in poly bottle

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).

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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