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C1625

Sigma-Aldrich

L-Canavanine

≥98% (TLC), powder, from Canavalia ensiformis

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Synonym(s):
L-α-Amino-γ-(guanidinooxy)-n-butyric acid
Empirical Formula (Hill Notation):
C5H12N4O3
CAS Number:
Molecular Weight:
176.17
MDL number:
PubChem Substance ID:
NACRES:
NA.26

biological source

Canavalia ensiformis

Quality Level

assay

≥98% (TLC)

form

powder

color

white to yellow

solubility

H2O: <100 mg/mL

application(s)

detection

storage temp.

2-8°C

SMILES string

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

InChI

1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1

InChI key

FSBIGDSBMBYOPN-VKHMYHEASA-N

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1 of 4

This Item
C9758G2253M9625
L-Canavanine &#8805;98% (TLC), powder, from Canavalia ensiformis

C1625

L-Canavanine

-
L-Canavanine sulfate salt &#8805;99% (TLC), powder

C9758

L-Canavanine sulfate salt

-
L-Glutamic acid &#947;-monohydroxamate

G2253

L-Glutamic acid γ-monohydroxamate

-
L-Methionine reagent grade, &#8805;98% (HPLC)

M9625

L-Methionine

Essential Grade
assay

≥98% (TLC)

assay

≥99% (TLC)

assay

≥97% (TLC)

assay

≥98% (HPLC)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

color

white to yellow

color

white

color

white to off-white

color

white

solubility

H2O: <100 mg/mL

solubility

H2O: 100 mg/mL

solubility

-

solubility

-

biological source

Canavalia ensiformis

biological source

plant seeds (Jack bean )

biological source

-

biological source

-

Biochem/physiol Actions

Canavanine is a naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). Overproduction of NO by iNOS plays a crucial role in the pathophysiology of septic shock and chronic inflammation.
A naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). Overproduction of NO by iNOS plays a crucial role in the pathophysiology of septic shock and chronic inflammation.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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E Arthur Bell
Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases, 10 Suppl 2, 21-25 (2009-12-16)
Because of the similarity of ALS/PDC symptoms to those of the paralytic disease lathyrism, cycad seeds from Guam were analyzed for the presence of the non-protein amino acid b-ODAP, which is known to cause lathyrism. Although b-ODAP was not detected
Ya-Lan Chang et al.
Antioxidants & redox signaling, 22(7), 587-602 (2014-10-21)
Mitochondrial succinate dehydrogenase (SDH) is an essential complex of the electron transport chain and tricarboxylic acid cycle. Mutations in the human SDH subunit D frequently lead to paraganglioma (PGL), but the mechanistic consequences of the majority of SDHD polymorphisms have
Junjie Tan et al.
Nature communications, 11(1), 629-629 (2020-02-02)
Base editors (BEs) are RNA-guided CRISPR-Cas-derived genome editing tools that induce single-nucleotide changes. The limitations of current BEs lie in their low precision (especially when multiple target nucleotides of the deaminase are present within the activity window) and their restriction
Nami Haruta et al.
Nucleic acids research, 40(17), 8406-8415 (2012-06-30)
UV radiation induces two major types of DNA lesions, cyclobutane pyrimidine dimers (CPDs) and 6-4 pyrimidine-pyrimidine photoproducts, which are both primarily repaired by nucleotide excision repair (NER). Here, we investigated how chronic low-dose UV (CLUV)-induced mutagenesis occurs in rad14Δ NER-deficient
Matthew D Berg et al.
G3 (Bethesda, Md.), 10(12), 4335-4345 (2020-10-22)
Non-proteinogenic amino acids, such as the proline analog L-azetidine-2-carboxylic acid (AZC), are detrimental to cells because they are mis-incorporated into proteins and lead to proteotoxic stress. Our goal was to identify genes that show chemical-genetic interactions with AZC in Saccharomyces

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