Glycosidic and peptidyl bond cleavage reactions of maltosylated carnosine

Xue Xia; Varoujan Yaylayan

doi:10.1016/j.foodchem.2025.145005

Glycosidic and peptidyl bond cleavage reactions of maltosylated carnosine

Food Chem. 2025 Jun 3:489:145005. doi: 10.1016/j.foodchem.2025.145005. Online ahead of print.

Authors

Xue Xia¹, Varoujan Yaylayan²

Affiliations

¹ School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Fengxian District, Shanghai, PR China.
² Department of Food Science and Agricultural Chemistry, McGill University, 21111 Lakeshore, Ste Anne de Bellevue, Quebec H9X 3V9, Canada. Electronic address: varoujan.yaylayan@mcgill.ca.

PMID: 40479999
DOI: 10.1016/j.foodchem.2025.145005

Abstract

The Maillard reaction of carnosine with maltose was performed using mechanochemistry, and the reaction mixture was analyzed using high-resolution tandem mass spectrometry in positive ionization mode. The MS/MS analysis of the Amadori compound of maltose and carnosine revealed that the protonated ion predominantly underwent glycosidic bond cleavage and characteristic dehydration reactions, while the sodiated ion exhibited mainly peptidyl and C2-C3 sugar bond cleavage reactions. The sugar-containing fragments in the MS/MS spectra were confirmed through isotope labelling experiments with U-¹³C₆-glycated carnosine. Under mechanochemical reaction conditions, both glycosidic and peptidyl bond cleavage were observed, leading to the formation of three additional Amadori compounds. In glucose/carnosine system, glycated carnosine was further reacted with glucose to produce N,N-di-glycated carnosine, in addition to glycated histidine, glycated β-alanine and N,N-di-glycated β-alanine, again demonstrating ease of peptidyl bond cleavages. These findings provide valuable insight into the potential role of peptides with disaccharides, contributing to the generation of multiple Amadori products.

Keywords: Glycated carnosine with maltose; Isotope labeling; MS/MS fragmentation; Mechanochemistry.