Influence of N Terminus Amino Acid on Peptide Cleavage in Solution through Diketopiperazine Formation.

ABSTRACT: Diketopiperazine (DKP) formation is an important degradation pathway for peptides and proteins. It can occur during synthesis and storage in either solution or the solid state. The kinetics of peptide cleavage through DKP formation have been analyzed for the model peptides Xaa¹-Pro²-Gly₄-Lys⁷ [Xaa = Gln, Glu, Lys, Ser, Phe, Trp, Tyr, Cha (β-cyclohexylalanine), Aib (α-aminoisobutyric acid), Gly, and Val] at multiple elevated temperatures in ethanol with ion mobility spectrometry-mass spectrometry (IMS-MS). When Xaa is an amino acid with a charged or polar side chain, degradation is relatively fast. When Xaa is an amino acid with a nonpolar alkyl side chain, the peptide is relatively stable. For these peptides, a bulky group on the α carbon speeds

SUBMITTER: Zhang ZC 

PROVIDER: S-EPMC10161955 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature