|
|
| | N-Benzyloxycarbonyl-D-aspartic acid Basic information |
| | N-Benzyloxycarbonyl-D-aspartic acid Chemical Properties |
| Melting point | 117 °C | | Boiling point | 472.8±45.0 °C(Predicted) | | density | 1.404±0.06 g/cm3(Predicted) | | refractive index | -10 ° (C=7, AcOH) | | storage temp. | Sealed in dry,2-8°C | | solubility | Methanol (Sparingly) | | pka | 3.75±0.23(Predicted) | | form | Solid | | color | White to Off-White | | Optical Rotation | Consistent with structure | | BRN | 2566464 | | Major Application | peptide synthesis | | InChI | 1S/C12H13NO6/c14-10(15)6-9(11(16)17)13-12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,18)(H,14,15)(H,16,17)/t9-/m1/s1 | | InChIKey | XYXYXSKSTZAEJW-SECBINFHSA-N | | SMILES | OC(=O)C[C@@H](NC(=O)OCc1ccccc1)C(O)=O | | CAS DataBase Reference | 78663-07-7(CAS DataBase Reference) |
| Safety Statements | 24/25 | | WGK Germany | 3 | | HS Code | 29242990 | | Storage Class | 13 - Non Combustible Solids |
| | N-Benzyloxycarbonyl-D-aspartic acid Usage And Synthesis |
| Chemical Properties | Off-White Solid | | Uses | A competitive inhibitor of indole-3-acetyl-L-aspartic acid hydrolase of Enterobacter agglomerans. | | reaction suitability | reaction type: solution phase peptide synthesis | | Synthesis | The general procedure for the synthesis of Cbz-D-aspartic acid from D-aspartic acid and benzyl chloroformate is as follows:
1. 6 M NaOH solution was added to 500 mL of distilled water at 0 °C and the pH of the solution was adjusted to 13. Subsequently, 65 g (489 mmol) of (R)-aspartic acid was added.
2. 141 g (831 mmol, 1.7 eq.) of benzyl chloroformate was slowly added to the above solution under magnetic stirring.
3. The reaction mixture was stirred at room temperature for 2 days. 4.
4. After completion of the reaction, the mixture was washed with ether and the aqueous phase was acidified with 6 N HCl to pH < 2. 5.
5. The acidified aqueous phase was extracted with ethyl acetate (AcOEt) and the organic phases were combined.
6. The organic phase was dried with anhydrous Na2SO4, filtered, and concentrated in a rotary evaporator to give 80 g of a clear, colorless gelatinous product in 59% yield.
Product Characterization:
- MS (ESI) m/e (MH+): 266
- 1H-NMR (CDCl3, 400 MHz): δ 7.21-7.21 (m, 5H), 6.14 (d, J = 8.4 Hz, 1H), 5.05 (s, 2H), 4.60 (m, 1H), 2.99 (m, 1H), 2.75 (m, 1H). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1040 - 1044
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 17, p. 2495 - 2511
[3] Asian Journal of Chemistry, 2013, vol. 25, # 11, p. 5948 - 5950
[4] Patent: WO2008/61208, 2008, A2. Location in patent: Page/Page column 31-32; 34-35
[5] Patent: US6660769, 2003, B1. Location in patent: Page column 13-14 |
| | N-Benzyloxycarbonyl-D-aspartic acid Preparation Products And Raw materials |
|