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 activity

Consistent with structure

BRN 

2566464

CAS DataBase Reference

78663-07-7(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

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

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