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30170

Sigma-Aldrich

L-Cysteic acid monohydrate

≥99.0% (T)

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Synonym(s):
(R)-2-Amino-3-sulfopropionic acid
Linear Formula:
HO3SCH2CH(NH2)CO2H·H2O
CAS Number:
Molecular Weight:
187.17
Beilstein/REAXYS Number:
3714036
MDL number:
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

≥99.0% (T)

form

powder or crystals

optical activity

[α]20/D +7.5±0.5°, c = 5% in H2O

technique(s)

LC/MS: suitable

color

white to faint yellow

mp

267 °C (dec.) (lit.)

solubility

H2O: soluble

application(s)

peptide synthesis

SMILES string

[H]O[H].N[C@@H](CS(O)(=O)=O)C(O)=O

InChI

1S/C3H7NO5S.H2O/c4-2(3(5)6)1-10(7,8)9;/h2H,1,4H2,(H,5,6)(H,7,8,9);1H2/t2-;/m0./s1

InChI key

PCPIXZZGBZWHJO-DKWTVANSSA-N

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This Item
30089C7477255300
vibrant-m

30170

L-Cysteic acid monohydrate

-
vibrant-m

30089

L-Cysteine

Premium Grade
vibrant-m

C7477

L-Cysteine hydrochloride

Essential+ Grade
vibrant-m

255300

3-Aminosalicylic acid

-
assay

≥99.0% (T)

assay

≥98.5% (RT)

assay

≥98.0%

assay

97%

technique(s)

LC/MS: suitable

technique(s)

HPLC: suitable

technique(s)

cell culture | mammalian: suitable

technique(s)

-

optical activity

[α]20/D +7.5±0.5°, c = 5% in H2O

optical activity

[α]20/D +8.0±0.5°, c = 5% in 5 M HCl

optical activity

-

optical activity

-

mp

267 °C (dec.) (lit.)

mp

240 °C (dec.) (lit.)

mp

174.1-174.7 °C

mp

240 °C (dec.) (lit.)

solubility

H2O: soluble

solubility

1 M HCl: 1 M at 20 °C, clear, colorless

solubility

H2O: 50 mg/mL

solubility

-

Application

Internal standard for amino acid analysis.

Biochem/physiol Actions

L-Cysteic acid is a sulfur containing aspartate analogue that may be used as a competitive inhibitor of the bacterial aspartate:alanine antiporter (AspT) exchange of aspartate and in other aspartate biological systems. L-Cysteic acid is used in monomeric surfactant development.
L-cysteic acid is an oxidation product of L-cysteine. L-Cysteic acid, an analogue of cysteine sulfinic acid, may be used in studies of excitatory amino acids in the brain, such as those that bind to cysteine sulfinic acid receptors. L-Cysteic acid is a useful agonist at several rat metabotropic glutamate receptors (mGluRs).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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B Meldrum
Epilepsia, 25 Suppl 2, S140-S149 (1984-01-01)
Amino acids provide the most universal and important inhibitory (gamma-aminobutyric acid (GABA), glycine) and excitatory (glutamate, aspartate, cysteic acid, cysteine sulphinic acid) neurotransmitters in the brain. An anticonvulsant action may be produced (1) by enhancing inhibitory (GABAergic) processes, and (2)
Internal standards for amino acid analysis.
J F Riordan et al.
Methods in enzymology, 47, 31-40 (1977-01-01)
Qi Shi et al.
The Journal of pharmacology and experimental therapeutics, 305(1), 131-142 (2003-03-22)
Moderate hyperhomocysteinemia is associated with several diseases, including coronary artery disease, stroke, Alzheimer's disease, schizophrenia, and spina bifida. However, the mechanisms for their pathogenesis are unknown but could involve the interaction of homocysteine or its metabolites with molecular targets such
A E Kingston et al.
Neuropharmacology, 37(3), 277-287 (1998-07-29)
Comparison of the pharmacological effects of a range of sulphur-containing amino acids on human mGluR1alpha and mGluR5a has been undertaken. cDNAs of each mGluR were transfected into a Syrian hamster tumour cell line AV12-664 that was previously transfected with the
Naoko Arashida et al.
Analytica chimica acta, 954, 77-87 (2017-01-14)
Amino acids and their related metabolites play important roles in various physiological processes and have consequently become biomarkers for diseases. However, accurate quantification methods have only been established for major compounds, such as amino acids and a limited number of

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