Synthesis of peptides containing various functions was efficiently accomplished by treatment of the tetrabutylammonium salts of N-protected amino acids (or peptides) with amino acid esters in the presence of bis(o- or p-nitrophenyl) phenylphosphonate. Synthesis of leucine-enkephalin was successfully achieved by the above method employing a (3+2) or (4+1) fragment coupling approach.
Reaction of carboxylate salts with cyclic phosphoramidates: amide bond formation by prior amine capture
作者:M. Wakselman、F. Acher
DOI:10.1016/s0040-4039(00)78585-6
日期:1980.1
Tri- or tetraalkyl-ammonium carboxylates react with 2-alkylamino-2-oxo-1,3,2-benzodioxaphospholes at 25°C to give amides or peptides, probably by a nucleophilic attack on phosphorous followed by a cascade of intramolecular acyl transfer reaction.