S. Girin, Y. Shvachkin
Jan 12, 2009
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Journal
International Journal of Peptide and Protein Research
Abstract
The interaction of N-protected amino acid active esters with imidazole has been found to be a reversible reaction. The rate constant values for a direct reaction of tert.-butyloxycarbonylglycine p-nitrophenyl ester with imidazole and for a reverse reaction of tert.-butyloxycarbonylglycine imidazolide with p-nitrophenol are reported. The effect of imidazole on the kinetics of active ester and imidazolide reactions with l-threonine methyl ester were studied. The influence of imidazole on the kinetics of O-acylation of N-benzyloxycarbonyl-l-serine amide was also investigated. The data obtained enable the optimum strategy to be chosen in the synthesis of peptides containing hydroxy-amino acid and histidine residues.