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21375

Sigma-Aldrich

L-Canavanine sulfate salt

≥98.0% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H12N4O3 · H2SO4
CAS Number:
2219-31-0
Molecular Weight:
274.25
Beilstein:
6121291
EC Number:
218-728-4
MDL number:
MFCD00012618
UNSPSC Code:
12352200
PubChem Substance ID:
24852798
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Assay

≥98.0% (TLC)

optical activity

[α]20/D +17±1°, c = 2% in H2O

mp

160-165 °C (dec.)

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

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Biochem/physiol Actions

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).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

A structural analog of L-arginine. Review: Biological effects and mode of action[1]

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Nicholas R Pannunzio et al.
Molecular cell, 68(5), 901-912 (2017-12-09)
DNA double-strand breaks (DSBs) occurring within fragile zones of less than 200 base pairs account for the formation of the most common human chromosomal translocations in lymphoid malignancies, yet the mechanism of how breaks occur remains unknown. Here, we have
G A Rosenthal
The Quarterly review of biology, 52(2), 155-178 (1977-06-01)
Many of the 200 or so non-protein amino acids synthesized by higher plants are related structurally to the constituents of common proteins. L-Canavanine, the guanidinooxy structural analogue of L-arginine, is representative of this group. It has provided valuable insight into

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