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Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures

Maillard reactions generate a wide array of amino acid- and sugar-derived intermediates; the isomeric mixtures of glycated amino acids are of particular interest. Excluding stereoisomers, regioisomers, and various anomers, most amino acids can form two monoglycated and three N,N-diglycated isomers w...

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Autores principales: Xing, Haoran, Yaylayan, Varoujan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8998915/
https://www.ncbi.nlm.nih.gov/pubmed/35408824
http://dx.doi.org/10.3390/ijms23073430
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author Xing, Haoran
Yaylayan, Varoujan
author_facet Xing, Haoran
Yaylayan, Varoujan
author_sort Xing, Haoran
collection PubMed
description Maillard reactions generate a wide array of amino acid- and sugar-derived intermediates; the isomeric mixtures of glycated amino acids are of particular interest. Excluding stereoisomers, regioisomers, and various anomers, most amino acids can form two monoglycated and three N,N-diglycated isomers when reacted with sugars during the Maillard reaction. Using synthetic Schiff bases and Amadori compounds as standards, we have demonstrated that diagnostic ions obtained from MS/MS fragmentations in negative ionization mode can be used effectively for the discrimination between glucose-derived Schiff bases and their corresponding Amadori compounds in both mono- and diglycated forms. The utilization of these diagnostic ions and isotopic labeling in the glycine/glucose model system revealed that milling glucose/glycine mixtures for 30 min/30 Hz at ambient temperature produced monoglycated glycine in equal proportions of Amadori and Schiff base forms, whereas diglycated glycine was a mixture of the three isomers: Schiff-Schiff, Schiff-Amadori, or Amadori-Amadori in approximately equal molar proportions. The above results were further corroborated using a synthetic histidine Amadori product, N,N-difructosyl-β-alanine, dipeptides, and ribose. Using mechanochemistry as a convenient synthetic tool in combination with MS/MS diagnostic ions, the isomeric diversity of the early stages of the Maillard reaction can be revealed.
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spelling pubmed-89989152022-04-12 Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures Xing, Haoran Yaylayan, Varoujan Int J Mol Sci Article Maillard reactions generate a wide array of amino acid- and sugar-derived intermediates; the isomeric mixtures of glycated amino acids are of particular interest. Excluding stereoisomers, regioisomers, and various anomers, most amino acids can form two monoglycated and three N,N-diglycated isomers when reacted with sugars during the Maillard reaction. Using synthetic Schiff bases and Amadori compounds as standards, we have demonstrated that diagnostic ions obtained from MS/MS fragmentations in negative ionization mode can be used effectively for the discrimination between glucose-derived Schiff bases and their corresponding Amadori compounds in both mono- and diglycated forms. The utilization of these diagnostic ions and isotopic labeling in the glycine/glucose model system revealed that milling glucose/glycine mixtures for 30 min/30 Hz at ambient temperature produced monoglycated glycine in equal proportions of Amadori and Schiff base forms, whereas diglycated glycine was a mixture of the three isomers: Schiff-Schiff, Schiff-Amadori, or Amadori-Amadori in approximately equal molar proportions. The above results were further corroborated using a synthetic histidine Amadori product, N,N-difructosyl-β-alanine, dipeptides, and ribose. Using mechanochemistry as a convenient synthetic tool in combination with MS/MS diagnostic ions, the isomeric diversity of the early stages of the Maillard reaction can be revealed. MDPI 2022-03-23 /pmc/articles/PMC8998915/ /pubmed/35408824 http://dx.doi.org/10.3390/ijms23073430 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Xing, Haoran
Yaylayan, Varoujan
Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures
title Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures
title_full Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures
title_fullStr Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures
title_full_unstemmed Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures
title_short Insight into Isomeric Diversity of Glycated Amino Acids in Maillard Reaction Mixtures
title_sort insight into isomeric diversity of glycated amino acids in maillard reaction mixtures
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8998915/
https://www.ncbi.nlm.nih.gov/pubmed/35408824
http://dx.doi.org/10.3390/ijms23073430
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