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L-Canavanine sulfate

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L-Canavanine sulfate Basic information

Product Name:
L-Canavanine sulfate
Synonyms:
  • canavanine sulphate
  • L-canavanine sulfate crystalline
  • L-Canavanine Sulfate, Canavalia ensiformis
  • l-α-amino-γ-(guanidinooxy)butyric acid sulfate salt
  • CANAVANINE SULFATE, L-(RG)
  • L-CANAVANINE SULFATE HYDRATE
  • L-CANAVANINE SULFATE
  • CANAVANINE SULFATE
CAS:
2219-31-0
MF:
C5H14N4O7S
MW:
274.25
EINECS:
218-728-4
Product Categories:
  • amino acid derivative
  • Amino Acids & Derivatives
  • Hydroxylamines (N-Substituted)
  • Amino Acids
  • Inhibitors
  • Nitric Oxide Reagents
  • Amino Acids
  • Biochemistry
  • Hydroxylamines
  • Hydroxylamines (O-Substituted)
  • non-Proteinorganic Amino Acids
  • chem-chemical
Mol File:
2219-31-0.mol
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L-Canavanine sulfate Chemical Properties

Melting point:
160-165 °C (dec.)
storage temp. 
2-8°C
solubility 
H2O: 100 mg/mL
form 
powder
color 
white
BRN 
6121291
Stability:
Hygroscopic
CAS DataBase Reference
2219-31-0(CAS DataBase Reference)
EPA Substance Registry System
L-Canavanine sulfate (2219-31-0)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
36-26
RIDADR 
2811
WGK Germany 
3
HS Code 
2925290090

MSDS

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L-Canavanine sulfate Usage And Synthesis

Uses

A Nitric Oxide Synthase inhibitor

Uses

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

Definition

ChEBI: An organic sulfate salt obtained by combining L-canavanine with one molar equivalent of sulfuric acid.

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.

Biological Activity

NO synthase inhibitor.

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.

Purification Methods

Recrystallise the sulfate by dissolving (~1g) in H2O (10mL), and adding with stirring 0.5 to 1.0 volumes of 95% EtOH whereby crystals separate. These are collected, washed with Me2CO/EtOH (1:1) and dried over P2O5 in a vacuum. [Hunt & Thompson Biochemical Preparations 13 416 1971, Feacon & Bell Biochem J 59 221 1955, Beilstein 4 III 1636, 4 IV 3188.]

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