High-Temperature, Solid-Phase Reaction of α-Amino Groups in Peptides with Lactose and Glucose: An Alternative Mechanism Leading to an α-Ketoacyl Derivative.

ABSTRACT: The reaction of proteins with reducing sugars results in the formation of Amadori products, which involves the N-terminal group and/or ε-amino group of the lysine side chain. However, less attention has been given to the reactivity of the N-terminus of a peptide chain under similar conditions. In our work, we focused on the reaction of the α-amino group of peptides in the presence of a reducing sugar, specifically lactose. We optimized the reaction conditions of model peptides with lactose in the solid phase and showed that temperatures above 120 °C lead to the deamination of the N-terminal amino acid moiety, ultimately resulting in α-ketoacids. We carried out detailed studies to confirm the structure of the deaminated product using analytical methods such as ESI-MS and LC-MS/MS, as well a

SUBMITTER: Kijewska M 

PROVIDER: S-EPMC10103172 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature