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C9758

Sigma-Aldrich

L-Canavanine sulfate salt

≥99% (TLC), powder

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C5H12N4O3 · H2SO4
Číslo CAS:
2219-31-0
Molekulová hmotnost:
274.25
Beilstein/REAXYS Number:
6121291
EC Number:
218-728-4
MDL number:
MFCD00012618
UNSPSC Code:
12352209
PubChem Substance ID:
24278349
NACRES:
NA.32

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)

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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).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

L-canavanine, a selective inhibitor of inducible NO synthase, increases plasma endothelin-1 concentrations in dogs with endotoxic shock
Mitaka C, et al.
Journal of Critical Care, 16(1), 17-23 (2001)
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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
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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
High-throughput transformation of Saccharomyces cerevisiae using liquid handling robots
Liu G, et al.
PLoS ONE, 12(3), e0174128-e0174128 (2017)
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