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Merck
CN

T173

Thio-L-citrulline

synthetic, solid

Synonym(s):

(S)-2-Amino-5-(thioureido)pentanoic acid, N5-Aminothioxomethyl-L-ornithine

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About This Item

Empirical Formula (Hill Notation):
C6H13N3O2S
CAS Number:
Molecular Weight:
191.25
UNSPSC Code:
12352204
Beilstein/REAXYS Number:
6844478
MDL number:
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biological source

synthetic

form

solid

color

white

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

N[C@@H](CCCNC(N)=S)C(O)=O

InChI

1S/C6H13N3O2S/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1

InChI key

BKGWACHYAMTLAF-BYPYZUCNSA-N

Biochem/physiol Actions

Potent and selective inhibitor of neuronal and endothelial isoforms of nitric oxide synthase.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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E S Furfine et al.
The Journal of biological chemistry, 269(43), 26677-26683 (1994-10-28)
Potent and selective inhibition of neuronal nitric oxide synthase (nNOS) compared to endothelial NOS (eNOS) and inducible NOS (iNOS) may be useful to treat cerebral ischemia (stroke) and other neurodegenerative diseases. S-Methyl-L-thiocitrulline (Me-TC) and S-ethyl-L-thiocitrulline (Et-TC) inhibited the oxidation of
H M Abu-Soud et al.
The Journal of biological chemistry, 269(51), 32318-32326 (1994-12-23)
Heme iron reduction in the nitric-oxide synthases (NOSs) requires calmodulin binding and is associated with increased NO synthesis and NADPH oxidation (Abu-Soud, H. M., and Stuehr, D. J. (1993) Proc. Natl. Acad. Sci., U. S. A. 90, 10769-10772). Here, we
C Frey et al.
The Journal of biological chemistry, 269(42), 26083-26091 (1994-10-21)
Nitric-oxide synthase (NOS) catalyzes the oxidation of L-arginine to citrulline and nitric oxide (NO). The enzyme is inhibited by a variety of N omega-monosubstituted L-arginine analogs, and some of these compounds are useful in reversing pathologies associated with the overproduction

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