3-cyano-L-alanine
3-CYANO-L-ALANINE · H-CPA-OH · (S)-2-Amino-3-cyanopropanoic acid · L-CNAla · H-ALA(3-CN)-OH · H-b-Cyano-Ala-OH · H-β-Cyano-Ala-OH · β-Cyano-L-Ala-OH
Identifikatoren & physikalische Daten
| CAS No. | 6232-19-5 |
|---|---|
| Summenformel | C4H6N2O2 |
| Durchschnittliche Molmasse | 114,1 g/mol |
| Monoisotopische Masse | 114,04292743 g/mol |
| SMILES | N#CC[C@H](N)C(=O)O |
| InChIKey | BXRLWGXPSRYJDZ-VKHMYHEASA-N |
| PubChem CID | 439742 |
| ChEMBL | CHEMBL4172293 |
| ChEBI | CHEBI:16934 |
| EC No. | 811-959-7 |
| DTXSID | DTXSID90977873 |
Chemische & physikalische Eigenschaften
| XLogP | -3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 87,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 134 |
| Schmelzpunkt | 217 °C |
| Lagerbedingungen | -20°C |
| Löslichkeit | PBS (pH 7.2): 10 mg/ml |
| Aggregatzustand | A crystalline solid |
| Farbe | White to yellow |
| InChI | 1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1 |
| InChIKey | BXRLWGXPSRYJDZ-VKHMYHEASA-N |
| SMILES | OC([C@@H](N)CC#N)=O |
Sicherheit & Vorschriften
| GHS-Einstufung | Not Classified |
|---|---|
| Hazard Classes and Categories | Not Classified |
| Wassergefährdungsklasse (WGK) | 3 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Hydrogen sulfide (H2S) is a naturally-occurring gasotransmitter with vasodilator and inflammatory modulating activity. H2S is synthesized naturally in a range of mammalian tissues principally by the activity of two enzymes, cystathionine γ lyase (CSE) and cystathionine β synthetase (CBS). β-cyano-L-Alanine (BCA) is a reversible inhibitor of the H2S-synthesizing enzyme CSE. BCA blocks H2S synthesis in rat liver preparations with an IC50 value of 6.5 μM and increases blood pressure in anaesthetized rats induced with hemorrhagic shock by inhibiting endogenous H2S synthesis. BCA at 50 mg/kg blocked both L-cysteine- and LPS-induced hyperalgesia in rats.
Verwenden
β-L-cyanoalanine is an amino acid that promotes seed germination in A. albus seeds. Beta-Cyano-L-alanine in the diet of adult locusts causes a decrease in the hemolymph volume thereby affecting water balance responses. L-β-cyanoalanine is an inhibitor of vitamin B6.