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Mechanochemical generation of Schiff bases and Amadori products and utilization of diagnostic MS/MS fragmentation patterns in negative ionization mode for their analysis.
Carbohydr Res. 2020 Sep; 495:108091.CR

Abstract

The use of tandem mass spectrometry under positive ionization mode was previously developed as a tool for distinguishing isomeric Schiff bases and Amadori products. In this paper, similar diagnostic MS/MS fragmentation patterns were identified under negative ionization mode and was utilized to study the composition of mechanochemically generated Maillard reaction mixtures. The major diagnostic ion of the Schiff base was found to be a diose attached to the amino acid residue, while that of the Amadori compound was a triose. The structures of the diagnostic ions were confirmed through isotope labeling technique and elemental composition. Furthermore, application of this technique showed that ball milling of glucose with different amino acids almost exclusively results in the formation of a mixture of Schiff bases and Amadori compounds, and that amino acids with basic side chains generated more Schiff bases and those with acidic side chains generated more Amadori products.

Authors+Show Affiliations

Department of Food Science & Agricultural Chemistry, McGill University, 21111, Lakeshore, Ste Anne de Bellevue, Quebec, H9X 3V9, Canada.Department of Food Science & Agricultural Chemistry, McGill University, 21111, Lakeshore, Ste Anne de Bellevue, Quebec, H9X 3V9, Canada. Electronic address: varoujan.yaylayan@mcgill.ca.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32807359

Citation

Xing, Haoran, and Varoujan Yaylayan. "Mechanochemical Generation of Schiff Bases and Amadori Products and Utilization of Diagnostic MS/MS Fragmentation Patterns in Negative Ionization Mode for Their Analysis." Carbohydrate Research, vol. 495, 2020, p. 108091.
Xing H, Yaylayan V. Mechanochemical generation of Schiff bases and Amadori products and utilization of diagnostic MS/MS fragmentation patterns in negative ionization mode for their analysis. Carbohydr Res. 2020;495:108091.
Xing, H., & Yaylayan, V. (2020). Mechanochemical generation of Schiff bases and Amadori products and utilization of diagnostic MS/MS fragmentation patterns in negative ionization mode for their analysis. Carbohydrate Research, 495, 108091. https://doi.org/10.1016/j.carres.2020.108091
Xing H, Yaylayan V. Mechanochemical Generation of Schiff Bases and Amadori Products and Utilization of Diagnostic MS/MS Fragmentation Patterns in Negative Ionization Mode for Their Analysis. Carbohydr Res. 2020;495:108091. PubMed PMID: 32807359.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Mechanochemical generation of Schiff bases and Amadori products and utilization of diagnostic MS/MS fragmentation patterns in negative ionization mode for their analysis. AU - Xing,Haoran, AU - Yaylayan,Varoujan, Y1 - 2020/07/19/ PY - 2020/05/21/received PY - 2020/06/14/revised PY - 2020/07/02/accepted PY - 2020/8/19/entrez PY - 2020/8/19/pubmed PY - 2021/6/1/medline KW - Amadori compound KW - Ball milling KW - Diagnostic ions KW - ESI negative mode KW - ESI-qToF-MS/MS KW - Maillard reaction KW - Mechanochemistry KW - Schiff base KW - Tandem mass spectrometry (MS/MS) SP - 108091 EP - 108091 JF - Carbohydrate research JO - Carbohydr Res VL - 495 N2 - The use of tandem mass spectrometry under positive ionization mode was previously developed as a tool for distinguishing isomeric Schiff bases and Amadori products. In this paper, similar diagnostic MS/MS fragmentation patterns were identified under negative ionization mode and was utilized to study the composition of mechanochemically generated Maillard reaction mixtures. The major diagnostic ion of the Schiff base was found to be a diose attached to the amino acid residue, while that of the Amadori compound was a triose. The structures of the diagnostic ions were confirmed through isotope labeling technique and elemental composition. Furthermore, application of this technique showed that ball milling of glucose with different amino acids almost exclusively results in the formation of a mixture of Schiff bases and Amadori compounds, and that amino acids with basic side chains generated more Schiff bases and those with acidic side chains generated more Amadori products. SN - 1873-426X UR - https://www.unboundmedicine.com/medline/citation/32807359/Mechanochemical_generation_of_Schiff_bases_and_Amadori_products_and_utilization_of_diagnostic_MS/MS_fragmentation_patterns_in_negative_ionization_mode_for_their_analysis_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(20)30314-1 DB - PRIME DP - Unbound Medicine ER -
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