Fmoc-Gly-OH
FMOC-GLY-OH · FMOC-GLY · FMOC-L-GLY-OH · FMOC-L-GLY · FMOC-GLYCINE · Fmoc-g · Fmoc-GL · Fomc-Gly-OH
Identifikatoren & physikalische Daten
| CAS No. | 29022-11-5 |
|---|---|
| Summenformel | C17H15NO4 |
| Durchschnittliche Molmasse | 297,3 g/mol |
| Monoisotopische Masse | 297,10010796 g/mol |
| SMILES | O=C(O)CNC(=O)OCC1c2ccccc2-c2ccccc21 |
| InChIKey | NDKDFTQNXLHCGO-UHFFFAOYSA-N |
| PubChem CID | 93124 |
| ChEMBL | CHEMBL5429058 |
| EC No. | 249-373-3 |
| DTXSID | DTXSID60183262 |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 75,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 403 |
| Polymers | Other Classes -> Polycyclic Aromatic Hydrocarbons |
| Physical Description | White powder[Sigma-Aldrich MSDS] |
| Schmelzpunkt | 174-175 °C(lit.) |
| Siedepunkt | 438.82°C (rough estimate) |
| Dichte | 1.1671 (rough estimate) |
| Brechungsindex | 1.4500 (estimate) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | almost transparency in Methanol |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 3.89±0.10(Predicted) |
| Farbe | White |
| BRN | 2163967 |
| Hauptanwendungen | peptide synthesis |
| InChI | InChI=1S/C17H15NO4/c19-16(20)9-18-17(21)22-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15H,9-10H2,(H,18,21)(H,19,20) |
| InChIKey | NDKDFTQNXLHCGO-UHFFFAOYSA-N |
| SMILES | C(O)(=O)CNC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O |
| CAS Datenbank | 29022-11-5(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 50% (5 of 10) of reports.WarningH302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 10 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Gefahrenübersicht | Not considered hazardous by GHS classification[Sigma-Aldrich MSDS] See 2-Acetylaminofluorene and Fluorene. |
| Hazard Classes and Categories | Acute Tox. 4 (20%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29242995 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Fmoc-Gly-OH is an N-Fmoc-protected form of Glycine (G615990). Glycine is a nonessential amino acid that acts as an inhibitory neyrotransmitter in the vertebrate central nervous system. Glycine also posesses cytoprotective against oxidant damage in the kidney.
Herstellung & Synthese
synthetische
Glycine (Gly) (0.5 g, 6.66 mmol) was dissolved in 10% NaCO3 (14 ml) under stirring in a 50-ml flask. To the resulting solution, which had been put into an ice bath, 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) (1.72 g, 6.66 mmol) in dioxane (12 ml) was gradually added. The reaction mixture was stirred at room temperature for 4 hours. Then added water (150 ml) to the mixture. The aqueous phase layer was separated from the reaction mixture and stripped with ether three times (75 ml×3). The stripped aqueous layer was acidified with 2N HCl aqueous solution to a pH=2, followed by extraction with ethyl acetate three times (75 ml×3). The organic phase layer was recovered and concentrated to obtain crude product of 1.70 g. The crude product was recrystallized in a mixed solvent of ethyl acetate hexane=1:2 (30 ml), and white solid denoted as Fmoc-Gly-OH was obtained after filtration at a reduced pressure.