Journal of the American Chemical Society

Peptide Synthesis from N-Carboxy-α-amino Acid Anhydrides in Water. Aminoacylpenicillanic Acids

NH Grant, HE Alburn

Index: Grant,N.H.; Alburn,H.E. Journal of the American Chemical Society, 1964 , vol. 86, p. 3870 - 3873

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Citation Number: 13

Abstract

The coupling in aqueous systems between N-carboxyanhydrides of amino acids (NCA's) and amino acids such as 6-arninopenicillanic acid (6-APA) can be controlled to give high yields of dipeptide. Minimization of rearrangement, polymerization, and hydrolysis reactions depends upon selection of a pH level and ratio of reactant concentrations capable of maintaining the total base strength of attacking 6-APA, established by both the pK2 and ...