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Merck

C9758

L-Canavanine sulfate salt

plant seeds (Jack bean ), ≥99% (TLC), iNOS inhibitor, powder

Sinónimos:

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

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C5H12N4O3 · H2SO4
Número CAS:
Peso molecular:
274.25
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
218-728-4
MDL number:
Beilstein/REAXYS Number:
6121291
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Nombre del producto

L-Canavanine sulfate salt, ≥99% (TLC), powder

InChI key

MVIPJKVMOKFIEV-DFWYDOINSA-N

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

SMILES string

OS(O)(=O)=O.N[C@@H](CCONC(N)=N)C(O)=O

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

Quality Level

Gene Information

human ... NOS2(4843)

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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).
Naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes; selective inhibitor of inducible nitric oxide synthase (iNOS).

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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