All Photos(2)

C2196

Sigma-Aldrich

L-Cysteine S-sulfate

≥98% (TLC)

Synonym(s):
S-Sulfo-L-cysteine
Empirical Formula (Hill Notation):
C3H7NO5S2
CAS Number:
Molecular Weight:
201.22
Beilstein:
1726832
MDL number:
PubChem Substance ID:

Quality Level

assay

≥98% (TLC)

form

powder

application(s)

ligand binding assay: suitable

color

white

storage temp.

−20°C

SMILES string

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

InChI

1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1

InChI key

NOKPBJYHPHHWAN-REOHCLBHSA-N

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Packaging

5 mg in glass bottle
25 mg in poly bottle

Biochem/physiol Actions

L-Cysteine S-sulfate (LCSS) is used as an NMDA glutamatergic receptor agonist. It serves as a substrate for cystine lyase(s).
Cysteine is one of the functional amino acids that are associated with growth, reproduction, maintenance and immunity. Cysteine is a source of disulfide linkage in protein and is associated with sulfur transport. At physiological pH, cysteine undergoes rapid oxidation to form cystine. Reduced availability of cysteine or cystine, influences leukocyte metabolism. L-Cysteine serves as a precursor for the rate limiting step in glutathione synthesis that occurs in neurons. It donates inorganic sulfate for detoxification reactions. Therefore, L-cysteine might be associated with neuroprotection. It is found to obstruct the entry of heavy metal ions across the blood-brain barrier into the brain. Increased levels of L-cysteine might lead to neurotoxicity.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C2196.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

R Nahum-Levy et al.
Biophysical journal, 80(5), 2152-2166 (2001-04-28)
Two distinct forms of desensitization have been characterized for N-methyl-D-aspartate (NMDA) receptors. One form results from a weakening of agonist affinity when channels are activated whereas the other form of desensitization results when channels enter a long-lived nonconducting state. A...
Desensitization of NMDA receptor channels is modulated by glutamate agonists.
Nahum-Levy R
Biophysical Journal, 80(5), 2152-2166 (2001)
Takeshi Nakatani et al.
Microbial cell factories, 11, 62-62 (2012-05-23)
Escherichia coli has two L-cysteine biosynthetic pathways; one is synthesized from O-acetyl L-serine (OAS) and sulfate by L-cysteine synthase (CysK), and another is produced via S-sulfocysteine (SSC) from OAS and thiosulfate by SSC synthase (CysM). SSC is converted into L-cysteine...
E C Ramírez et al.
Journal of agricultural and food chemistry, 47(6), 2218-2225 (2000-05-04)
Cystine lyase is the enzyme responsible for off-aroma deterioration in fresh unblanched broccoli. In this research, cystine lyase purification from broccoli has been optimized. Only one protein peak with cystine lyase activity was found during purification. Broccoli cystine lyase was...
Studies on analogues of L-cysteine and L-cystine. III. The effect of selenium cystine on leukemia.
WEISBERGER AS and SUHRLAND LG.
Blood, 11(1), 19-30 (1956)

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