77434-01-6

Upstream product

• 79-08-3 bromoacetic acid 
• 501-53-1 benzyl chloroformate 
• 5366-33-6 H-L-Val-OEt*TosOH 
• 95015-88-6 ethyl N-(t-butoxycarbonylmethyl)-L-valinate 
• 77328-37-1 ethyl N-carboxymethyl-L-valinate 

Downstream Products

• 77434-05-0 Z-Cm(L-Pro-O-t-Bu)-L-Val-OEt 
• 100689-89-2 (S)-2-(Benzyloxycarbonyl-{2-[(S)-2-((S)-1-tert-butoxycarbonyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-amino)-3-methyl-butyric acid ethyl ester 
• 77434-38-9 (S)-2-(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-methyl-butyric acid ethyl ester 
• 77434-18-5 (S)-2-(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-methyl-butyric acid 
• 77434-19-6 (S)-1-{2-[Benzyloxycarbonyl-((S)-1-carboxy-2-methyl-propyl)-amino]-acetyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 100689-92-7 Z-L-Phe-Cm(-L-Pro-L-Val-O-t-Bu)-L-Val-OEt 
• 100690-02-6 Z-Cm(L-Pro-L-Val-L-Phe-O-t-Bu)-L-Val-OEt 

Relevant academic research and scientific papers

Studies of Unusual Amino Acids and Their Peptides. XVII. The Synthesis of Peptides Containing N-Carboxymethyl Amino Acids. II.

The synthetic routes were investigated to four kinds of tetrapeptides made up of three usual amino acid residues and one N-carboxymethyl (Cm-) amino acid residue.The application of vacuum distillation made the isolation of a Cm-amino acid diester more convenient and efficient compared with the chromatographic methods which had been used previously.The efficiency of peptide bond formation at the imino group of a Cm-amino acid by the acid chloride method was remarkably improved under suitable reaction conditions.In the elongation of the peptide chain from a peptide containing a Cm-amino acid at the C-terminal position, the coupling efficiency was usually poorer than that in the case of the corresponding peptide composed only of the usual amino acid residues, and it depended greatly on the coupling methods, the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-1-hydroxybenzotriazole method being generaly the most desirable.

Studies of Unusual Amino Acids and Their Peptides. XIII. The Chemistry of N-(Carboxymethyl)amino Acids. II. The Synthesis of Peptides Containing N-(Carboxymethyl)amino Acids

The basic problems in the synthesis of peptides with N-carboxymethyl(Cm-)amino acids were investigated.Several kinds of N-protected derivatives of a free Cm-amino acid and the N-benzyloxycarbonyl (Z) derivative of its monoester were obtained by the conven