2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside
2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside · 2,4-Dinitrophenyl 2-Deoxy-2-fluoro- · 2',4'-dinitrophenyl 2-deoxy-2-fluorogalactopyranoside · β-D-Galactopyranoside, 2,4-dinitrophenyl 2-deoxy-2-fluoro- · 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside, CAS 143716-62-5
Identifiers & Physical Properties
| CAS No. | 143716-62-5 |
|---|---|
| Molecular formula | C12H13FN2O9 |
| Average molar mass | 348.24 g/mol |
| Monoisotopic mass | 348.06050816 g/mol |
| SMILES | O=[N+]([O-])c1ccc(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2F)c([N+](=O)[O-])c1 |
| InChIKey | UFSBFVZQJZMIOU-RMPHRYRLSA-N |
| PubChem CID | 3083384 |
| DTXSID | DTXSID10162527 |
Chemical & Physical Properties
| XLogP | 0.3 |
|---|---|
| Topological polar surface area | 171 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 10 |
| Rotatable bonds | 3 |
| Heavy atoms | 24 |
| Formal charge | 0 |
| Complexity | 470 |
| Melting point | 168-170°C |
| Boiling point | 615.736±55.00 °C(Press: 760.00 Torr)(predicted) |
| Density | 1.692±0.10 g/cm3(Temp: 25 °CPress: 760 Torr)(predicted) |
| Storage conditions | Amber Vial, Refrigerator |
| Solubility | Methanol (Slightly) |
| Physical state | Solid |
| pKa (acidity coefficient) | 12.190±0.70(predicted) |
| Color | Off-White to Pale Yellow |
Applications & Uses
Uses
Fluorinated and deoxygenated glycosides as mechanistic probes of Escherichia coli (lacZ) β-galactosidase. By use of the slow substrate 2,4-dinitrophenyl-2-deoxy-2-fluoro-β-D-galactopyranoside, a glycosyl enzyme intermediate has been trapped on the enzyme. Glu-268 was identified as the catalytic nucleophile of human lysosomal β-galactosidase precursor.
Uses
2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside is fluorinated and deoxygenated glycosides as mechanistic probes of Escherichia coli (lacZ) β-galactosidase. By use of the slow substrate 2,4-dinitrophenyl-2-deoxy-2-fluoro-β-D-galactopyranoside, a glycosyl enzyme intermediate has been trapped on the enzyme.