Tetrahedron

Study of intramolecular aminolysis in peptides containing N-alkylamino acids at position 2

VV Ryakhovsky, AS Ivanov

Index: Ryakhovsky, Vladimir V.; Ivanov, Andrey S. Tetrahedron, 2012 , vol. 68, # 35 p. 7070 - 7076

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Abstract

Many peptides and proteins, containing Nα-alkylamino acids (including proline) at the second position, are prone to intramolecular aminolysis (IA) with elimination of N-terminal dipeptide sequence as 2, 5-diketopiperazines (DKP). We synthesized a series of short peptides, containing N-alkylamino acids at position 2, and studied their stability in the presence of acetic acid and amines. The presence of side chains in the second and the ...