C9758

Sigma-Aldrich

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:
Molecular Weight:
274.25
Beilstein/REAXYS Number:
6121291
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32
Pricing and availability is not currently available.

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.NC@@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)

Looking for similar products? Visit Product Comparison Guide

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

20/21/22

Safety Statement

36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Systematic gene-to-phenotype arrays: a high-throughput technique for molecular phenotyping
Jaeger PA, et al.
Molecular Cell, 69(2), 321-333 (2018)
Cyanamide is biosynthesized from l-canavanine in plants
Kamo T, et al.
Scientific reports, 5, 10527-10527 (2015)
Kellyn M Hoffert et al.
Genetics, 213(1), 97-112 (2019-07-20)
Maintenance of genome integrity is a crucial cellular focus that involves a wide variety of proteins functioning in multiple processes. Defects in many different pathways can result in genome instability, a hallmark of cancer. Utilizing a diploid Saccharomyces cerevisiae model...
Osama Mansour et al.
Current genetics, 66(3), 577-592 (2020-01-15)
Mutations in budding yeast occur in meiosis at higher frequencies than in cells grown vegetatively. In contrast to mutations that occur in somatic cells, meiotic mutations have a special, long-range impact on evolution, because they are transferred to the following...
Jun Akaogi et al.
Autoimmunity reviews, 5(6), 429-435 (2006-08-08)
Association of SLE and alfalfa was first reported in a volunteer who developed lupus-like autoimmunity while ingesting alfalfa seed for a hypercholesterolemia study. This was corroborated with studies in monkeys fed with alfalfa sprout that developed SLE. Re-challenge with L-canavanine...

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.