Cbz-beta-Amino-L-alanine Chemical Properties

Melting point:

~240 °C (dec.)

alpha 

-39 º (1%, 1N HCl)

Boiling point:

463.8±45.0 °C(Predicted)

Density 

1.303±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in dilute acid.

form 

Solid

pka

2.86±0.16(Predicted)

color 

White

optical activity

[α]20/D 39±1°, c = 1% in 1 M HCl

Sensitive 

Hygroscopic

BRN 

4486950

InChI

InChI=1S/C11H14N2O4/c12-6-9(10(14)15)13-11(16)17-7-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1

InChIKey

FOXRXVSTFGNURG-VIFPVBQESA-N

SMILES

C(O)(=O)[C@H](CN)NC(OCC1=CC=CC=C1)=O

CAS DataBase Reference

35761-26-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

3

HS Code 

2922.49.3700

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

Cbz-beta-Amino-L-alanine Usage And Synthesis

Chemical Properties

White Solid

Uses

Nalpha-Benzyloxycarbonyl-L-2,3-diaminopropionic acid is a important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of N(alpha)-Z-L-2,3-diaminopropionic acid from (S)-2-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propionic acid is as follows: 50 g of (S)-N-benzyloxycarbonyl-N'-tert-butoxycarbonyl-2,3-diaminopropionic acid was dissolved in 500 mL of methylene chloride, followed by 50 mL of trifluoroacetic acid. The reaction mixture was stirred at 50 °C for the reaction and subsequently left at room temperature overnight. Upon completion of the reaction, the reaction mixture was concentrated to dryness by rotary evaporator and the evaporation process was repeated to completely remove the solvent.

References

[1] Collection of Czechoslovak Chemical Communications, 1976, vol. 41, p. 2969 - 2977
[2] Patent: CN108452321, 2018, A. Location in patent: Paragraph 0113; 0114; 0115; 0116

Cbz-beta-Amino-L-alanine(35761-26-3)Related Product Information

• L-N-Cbz-3-N-Boc-Amino-alanine
• Boc-Dap-OH
• (S)-3-AMINO-2-CBZ-AMINO-PROPIONIC ACID TERT-BUTYL ESTER
• AC-HIS-OH H2O
• Fmoc-Lys(Boc)-OH
• Z-DAP(FMOC)-OH
• Cbz-beta-Amino-L-alanine
• (S)-N-4-BOC-N-1-CBZ-2-PIPERAZINE CARBOXYLIC ACID
• (S)-Methyl 2-N-Cbz-3-N-Boc-propanoate
• CBZ-BETA-AMINO-D-ALANINE
• L-Alanine
• L-2,3-Diaminopropionic acid
• DL-2-AMINOPROPIONIC ANHYDRIDE
• 2,3-Diaminopropionic acid
• METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE
• Z-DAP(Z)-OH
• (S)-(-)-2-OXO-1,5-IMIDAZOLIDINEDICARBOXYLIC ACID 1-BENZYL ESTER
• Z-L-DAP(BOC)-OBN