| Identification | Back Directory | [Name]
L-CYSTEINESULFINIC ACID MONOHYDRATE | [CAS]
207121-48-0 | [Synonyms]
3-sulfino-l-alanine
L-Cysteinesulfinic Acid (hydrate)
(2R)-2-aMino-3-sulfinopropanoic acid
L-Cysteinesulfinic acid Monohydrate 99%
(1R)-1-amino-2-mercaptoethanesulfinic acid hydrate | [EINECS(EC#)]
623-116-9 | [Molecular Formula]
HO2SCH2CH(NH2)CO2HH2O | [MDL Number]
MFCD00150732 | [MOL File]
207121-48-0.mol | [Molecular Weight]
171.17 |
| Chemical Properties | Back Directory | [Melting point ]
163 °C (dec.)(lit.)
| [storage temp. ]
-20°C | [solubility ]
Aqueous Acid (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Optical Rotation]
[α]25/D +24°, c = 1 in 1 M HCl | [Stability:]
Temperature Sensitive | [Major Application]
peptide synthesis | [InChI]
1S/C3H7NO4S.H2O/c4-2(3(5)6)1-9(7)8;/h2H,1,4H2,(H,5,6)(H,7,8);1H2/t2-;/m0./s1 | [InChIKey]
YQIXTMZYGQXTCZ-DKWTVANSSA-N | [SMILES]
[H]O[H].N[C@@H](CS(O)=O)C(O)=O |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3
| [HS Code ]
2930901300 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
L-Cysteinesulfinic acid is an excitatory amino acid and agonist of metabotropic glutamate receptors (mGluRs).1,2 It increases intracellular inositol phosphate levels in CHO cells expressing mGluR1, mGluR5, or mGluR8 (EC50s = 120, 30, and 110 μM, respectively) and inhibits forskolin-induced cAMP production in CHO cells expressing mGluR2 or mGluR6 and hamster kidney cells expressing mGluR4 (EC50s = 100, 100, and 2,000 μM, respectively).2 It selectively binds to mGluR1α (Ki = 3,510 nM) over adrenergic, dopamine, histamine, muscarinic, nicotinic, or serotonin receptors (Kis = >10,000 nM for all). L-Cysteinesulfinic acid (1 mM) decreases mean arterial blood pressure and heart rate in rats when microinjected into the nucleus tractus solitarius (NTS).1 L-Cysteinesulfinic acid can be formed via oxidation of L-cysteine by reactive oxygen species (ROS), and conversion of cysteine to L-cysteinesulfinic acid in cysteine-containing peptide probes has been used to measure oxidative stress.3 | [Chemical Properties]
Off-White Solid | [Uses]
An amino acid derivative with neuropathological interest; Putative excitatory amino acid neurotransmitter. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Biochem/physiol Actions]
Cysteinesulfinic acid (CSA), also called 3-sulfinoalanine is synthesized by the conversion of sulfur to sulfinic acid in cysteine by the enzyme cysteine dioxygenase (CDO). CSA is a putative excitatory amino acid (EAA) with neurotransmitter functionality. It also regulates cardiovascular functions. | [References]
[1] TAKEMOTO Y. Cardiovascular actions of l-cysteine and l-cysteine sulfinic acid in the nucleus tractus solitarius of the rat[J]. Amino Acids, 2014, 46 7: 1707-1713. DOI: 10.1007/s00726-014-1733-z
[2] QI SHI. L-homocysteine sulfinic acid and other acidic homocysteine derivatives are potent and selective metabotropic glutamate receptor agonists.[J]. Journal of Pharmacology and Experimental Therapeutics, 2003, 305 1: 131-142. DOI: 10.1124/jpet.102.047092
[3] CHUN-LAN KENG. Design of Peptide-Based Probes for the Microscale Detection of Reactive Oxygen Species[J]. Analytical Chemistry, 2017, 89 20: 10883-10888. DOI: 10.1021/acs.analchem.7b02544 |
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| Company Name: |
Energy Chemical
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| Tel: |
021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Sigma-Aldrich
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| Tel: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
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