Identification of MS/MS diagnostic ions to distinguish Schiff bases of Nα- or Nε-mono-glycated and Nα,Nε-di-glycated lysines from their Amadori isomers

Lysine is the principal amino acid that participates in the Maillard reaction between polypeptides and reducing sugars in foods and in vivo. For mechanistic studies of the early Maillard reaction, diagnostic MS/MS fragmentations have been recently employed to discriminate between Amadori rearrangeme...

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Bibliographic Details
Published in:European food research & technology 2022-11, Vol.248 (11), p.2753-2763
Main Authors: Xing, Haoran, Mossine, Valeri V., Yaylayan, Varoujan
Format: Article
Language:English
Subjects:
Adducts
Agriculture
Amadori compounds
Amino acids
Analytical Chemistry
Biotechnology
Chemistry
Chemistry and Materials Science
Diagnostic systems
Food Science
Forestry
Identification methods
Imines
In vivo methods and tests
Ionization
Isomers
Lysine
Maillard reaction
Original Paper
Polypeptides
Spectrometry
Sugar
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Summary:Lysine is the principal amino acid that participates in the Maillard reaction between polypeptides and reducing sugars in foods and in vivo. For mechanistic studies of the early Maillard reaction, diagnostic MS/MS fragmentations have been recently employed to discriminate between Amadori rearrangement products (ARP) and Schiff bases of glycated aliphatic amino acids. However, the utility of this method to identify ARP and Schiff bases of glycated dibasic amino acids, such as lysine, has not been explored yet. In this study, we report the potential of MS/MS fragmentations in the negative ionization mode to distinguish Schiff bases of N α , N ε -diglycated lysines from their Amadori isomers, as well as utilization of 15  N-labeled lysines and the MS/MS fragmentations under positive ionization mode to distinguish between the N α - and N ε -regioisomers of mono-glycated lysine. The applicability of this approach is exemplified in a mass-spectrometric analysis of a solid-state reaction between lysine and glucose in a ball mill. The analysis of the MS/MS fragmentation pattern of the glycated adduct has revealed the simultaneous formation of mono-glycated adducts, mainly N ε -Schiff bases, and di-glycated adducts, predominantly a mixture of N α , N ε -Schiff–Schiff and N α , N ε -Schiff–Amadori isomers.
ISSN:1438-2377
1438-2385
DOI:10.1007/s00217-022-04083-y