H-GLY-GLY-PHE-OH CAS#: 6234-26-0; 凯望编码 (ChemWhat Code): 87189
Identification
| 英文名 | H-GLY-GLY-PHE-OH CAS#: 6234-26-0 |
| IUPAC Name | (2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoic acid |
| 分子结构 |  |
| CAS编号 | 6234-26-0 |
| MDL Number | MFCD00066054 |
| 别名 | H-GLY-GLY-PHE-OH 6234-26-0 gly-gly-phe (S)-2-(2-(2-Aminoacetamido)acetamido)-3-phenylpropanoic acid glycylglycyl-L-phenylalanine L-N-(N-Glycylglycyl)-3-phenylalanine CHEBI:73905 glycylglycylphenylalanine CHEMBL1221711 Alanine, N-(N-glycylglycyl)-3-phenyl-, L- (2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoic acid Glycyl-glycyl-L-phenylalanine (2S)-2-[2-(2-AMINOACETAMIDO)ACETAMIDO]-3-PHENYLPROPANOIC ACID MFCD00066054 Gly-Gly-L-Phe Glycyl-glycyl-phenylalanine SCHEMBL2032499 DTXSID301308519 BDBM50485553 AKOS010420259 AS-56826 CS-0134043 NS00060584 F88056 Q27144231 |
| 分子式 | C13H17N3O4 |
| 分子量 | 279.29 |
| InChI | InChI=1S/C13H17N3O4/c14-7-11(17)15-8-12(18)16-10(13(19)20)6-9-4-2-1-3-5-9/h1-5,10H,6-8,14H2,(H,15,17)(H,16,18)(H,19,20)/t10-/m0/s1 |
| InChI Key | KAJAOGBVWCYGHZ-JTQLQIEISA-N |
| Isomeric SMILES | C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)CNC(=O)CN |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US5286637 | Biologically active drug polymer derivatives and method for preparing same | 1994 |
| US4727061 | Pharmaceutical preparations having diuretic activity | 1988 |
Physical Data
| Appearance | White powder |
| Melting Point, °C |
| 222 – 223 |
| 228 – 230 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C |
| Chemical shifts, Spectrum | 1H | CD3OD | |
| Chemical shifts, Spectrum | 13C | CD3OD | |
| Spectrum | 1H | heavy water | |
| Chemical shifts | 1H | D2O | 29.84 |
| 1H | D2O | 29.84 | |
| Chemical shifts | 13C | D2O | 29.84 |
| Chemical shifts | 1H | dimethylsulfoxide-d6 |
| H-GLY-GLY-PHE-OH CAS#: 6234-26-0 NMR |  |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Comment (UV/VIS Spectroscopy) |
| Spectrum | various solvent(s) | 250 – 267 nm |
Route of Synthesis (ROS)
| Conditions | Yield |
| ith sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 0 – 20℃; Experimental Procedure 8 Step 8. Synthesis of Compound 89 To a stirred mixture of (2S)-2-[2-(2-aminoacetamido)acetamido]-3-phenylpropanoic acid (Compound 88, 2.00 g, 7.16 mmol, 1.00 equiv) and NaHCO3 (1.80 g, 21.41 mmol, 3.00 equiv) in FLO (40.00 mL) were added BOC2O (1.86 g, 8.52 mmol, 1.20 equiv) in DMF (40.00 mL) dropwise at 0°C. The resulting mixture was stirred for overnight at room temperature. LCMS indicated the reaction was completed. The reaction was quenched with water at room temperature. The resulting mixture was extracted with EtOEt (3 x 50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse flash chromatography with the following conditions: column, C18 silica gel; mobile phase, ACN water(0.05% TFA), 5% to 60% gradient in 30 min; detector, UV 220 nm. This resulted in (2S)-2-(2-[2-[(tert-butoxycarbonyl)amino]acetamido]acetamido)-3-phenylpropanoic acid (Compound 89, 1.8 g, 60%) as a white semi-solid. LCMS (ESI,ms):380[M+H]+,324[M+H-56]+. 1HNMR:(300MHz, DMSO-d6) δ 8.17(d, J=8.1Hz, 1H), 7.93(t, J=5.7Hz, 1H), 7.31-7.20(m, 5H), 7.00(t, J =6.0Hz, 1H), 4.46-4.39(m, 1H),3.78-3.67(m, 2H), 3.56(d, J =5.7Hz, 2H), 3.09-3.02(m, 1H), 2.92-2.73(m, 1H), 1.39(s, 9H). | 60% |
| With sodium hydroxide In tetrahydrofuran for 3h; Ambient temperature; | |
| With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 0 – 20℃; Inert atmosphere; | 1.8g |
Safety and Hazards
| GHS Hazard Statements | Not Classified |
Source: European Chemicals Agency (ECHA)
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License URL: https://echa.europa.eu/web/guest/legal-notice
Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database
Other Data
| HS Code | |
| Storage | Store at 2–8°C, under vacuum for long time |
| Shelf Life | 1 year |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 279.296 |
| logP | -3.035 |
| HBA | 7 |
| HBD | 4 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 121.52 |
| Rotatable Bond (RotB) | 9 |
| Matching Veber Rules | 2 |
| Use Pattern |
| It is a tripeptide consisting of glycine, glycine, and phenylalanine, with the sequence Gly-Gly-Phe. It has several noteworthy properties and potential uses, particularly in the field of peptide drug development. This tripeptide is commonly studied as a fragment of larger peptide drugs. It serves as a modular building block for synthesizing biologically active peptides with therapeutic applications. |
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