L-Cysteic acid monohydrate

Name: <SC>L</SC>-Cysteic acid monohydrate
Brand: SIGMA

≥99.0% (T), suitable for LC/MS

Synonym(s):

(R)-2-Amino-3-sulfopropionic acid

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About This Item

Linear Formula:

HO₃SCH₂CH(NH₂)CO₂H·H₂O

CAS Number:

23537-25-9

Molecular Weight:

187.17

Beilstein:

3714036

MDL number:

MFCD00149544

UNSPSC Code:

12352209

PubChem Substance ID:

24858207

NACRES:

NA.26

Key Documents

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Product Name

L-Cysteic acid monohydrate, ≥99.0% (T)

Quality Level

200

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	30089	30095	C7477
Sigma-Aldrich 30170 L-Cysteic acid monohydrate	Sigma-Aldrich 30089 L-Cysteine	Sigma-Aldrich 30095 D-Cysteine	Sigma-Aldrich C7477 L-Cysteine hydrochloride
form powder or crystals	form powder or crystals	form powder or crystals	form powder or crystals
technique(s) LC/MS: suitable	technique(s) HPLC: suitable	technique(s) -	technique(s) cell culture \| mammalian: suitable
assay ≥99.0% (T)	assay ≥98.5% (RT)	assay ≥99% (RT)	assay ≥98.0%
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level 200
color white to faint yellow	color white	color -	color white to off-white
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 [α]20/D −7.6±1.0°, c = 5% in 5 M HCl	optical activity -

Application

Internal standard for amino acid analysis.[1]

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 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

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Amino acid neurotransmitters and new approaches to anticonvulsant drug action.

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)

L-homocysteine sulfinic acid and other acidic homocysteine derivatives are potent and selective metabotropic glutamate receptor agonists.

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

Sulphur-containing amino acids are agonists for group 1 metabotropic receptors expressed in clonal RGT cell lines.

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

Internal standards for amino acid analysis.

J F Riordan et al.

Methods in enzymology, 47, 31-40 (1977-01-01)

Highly sensitive quantification for human plasma-targeted metabolomics using an amine derivatization reagent.

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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