D-Serin
H-D-SER-OH · 2-AMINO-3-HYDROXYPROPANOIC ACID · D-Serin · (R)-2-amino-3-hydroxypropanoic acid · (R)-Serine · β-Hydroxyalanine · (R)-2-AMINO-3-HYDROXYPROPIONIC ACID · Methyl (2R)-3-hydroxy-2-(2,2,2-trifluoroacetaMido)propanoate
Identifikatoren & physikalische Daten
| CAS No. | 312-84-5 |
|---|---|
| Summenformel | C3H7NO3 |
| Durchschnittliche Molmasse | 105,09 g/mol |
| Monoisotopische Masse | 105,04259308 g/mol |
| SMILES | N[C@H](CO)C(=O)O |
| InChIKey | MTCFGRXMJLQNBG-UWTATZPHSA-N |
| PubChem CID | 71077 |
| ChEMBL | CHEMBL285123 |
| ChEBI | CHEBI:16523 |
| EC No. | 206-229-4 |
| DTXSID | DTXSID9041021 |
| Lokaler Name | D-Serin |
Chemische & physikalische Eigenschaften
| XLogP | -3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 83,6 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 72,6 |
| Löslichkeit | 364 mg/mL at 20 °CH2O: 0.1 g/mL, clear, colorless346 g/L (20 ºC) |
| Schmelzpunkt | 229 °C220 °C |
| Physical Description | Solid |
| Siedepunkt | 197.09°C (rough estimate) |
| Dichte | 1.3895 (rough estimate) |
| Brechungsindex | 1.4368 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (Säurekonstante) | 2.16±0.10(Predicted) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White |
| Merck | 14,8460 |
| BRN | 1721403 |
| Hauptanwendungen | cell analysis |
| InChI | 1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1 |
| InChIKey | MTCFGRXMJLQNBG-UWTATZPHSA-N |
| SMILES | N[C@H](CO)C(O)=O |
| LogP (Verteilungskoeffizient) | -1.490 (est) |
| CAS Datenbank | 312-84-5(CAS DataBase Reference) |
| EPA chemische Informationen | D-Serine (312-84-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 90% (18 of 20) of all reports.WarningH315 (10%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 20 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 19-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/21814D-Serine: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (10%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29225000 |
| RTECS-Nr. | VT8200000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Serine is one of the 20 naturally-occurring amino acids used by all organisms in the biosynthesis of proteins. Having a single chiral center, serine can exist as one of two stereoisomers (L-Serine and D-Serine).D-serine is categorized as a nootropic. It is an amino acid found in the brain and is produced primarily in astrocytes; the conversion of L-serine to D-serine is catalyzed by the serine racemase enzyme. D-serine acts as a co-agonist of glutamate NMDA receptors and binds at the glycine site. NMDA receptors mediate synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition, and learning. Schizophrenia is characterized by reduced NMDA receptor signaling and therefore, D-serine supplementation has been tested extensively in patients with schizophrenia. It is thought to improve cognitive symptoms in this population. It is worth noting that in Alzheimer’s disease, there is excess glutamate receptor activation. Memantine, one of the drugs used to treat Alzheimer’s disease, is an NMDA receptor antagonist.
Verwenden
D-Serine is involved in the biosynthesis of purines, pyrimidines, and other amino acids. D-Serine also is an agonist of glycine site of the NMDA-type glutamate receptor. It also acts as Lacosamide intermediate.