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
