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T173

Sigma-Aldrich

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:
156719-37-8
Molecular Weight:
191.25
Beilstein:
6844478
MDL number:
MFCD00935993
UNSPSC Code:
12352204

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

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Biochem/physiol Actions

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

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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