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C2196

Sigma-Aldrich

L-Cysteine S-sulfate

≥98% (TLC), suitable for ligand binding assays

Synonym(s):

S-Sulfo-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C3H7NO5S2
CAS Number:
1637-71-4
Molecular Weight:
201.22
Beilstein/REAXYS Number:
1726832
MDL number:
MFCD00133440
UNSPSC Code:
12352209
PubChem Substance ID:
24892471
NACRES:
NA.26

product name

L-Cysteine S-sulfate, ≥98% (TLC)

Quality Level

200

assay

≥98% (TLC)

form

powder

technique(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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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Claus Jacob et al.
Angewandte Chemie (International ed. in English), 42(39), 4742-4758 (2003-10-17)
Sulfur and selenium occur in proteins as constituents of the amino acids cysteine, methionine, selenocysteine, and selenomethionine. Recent research underscores that these amino acids are truly exceptional. Their redox activity under physiological conditions allows an amazing variety of posttranslational protein
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