215376-79-7Relevant articles and documents
Diagnostic MS/MS fragmentation patterns for the discrimination between Schiff bases and their Amadori or Heyns rearrangement products
Xing, Haoran,Mossine, Valeri V.,Yaylayan, Varoujan
, (2020)
Schiff bases, the Amadori and Heyns rearrangement products are the most important isomeric intermediates involved in the early Maillard reaction; distinguishing between them by analytical mass spectroscopic techniques remains a challenge. Here we demonstrate that MS/MS fragmentation patterns can be used for the discrimination between glucose derived Schiff bases, Amadori, and Heyns compounds with glycine. An ESI-qTOF-MS system operated in the positive mode under both acidic and neutral conditions was employed to generate unique MS/MS fragmentation patterns of the molecules. Analysis of the MS data has indicated that acidic medium is suitable for generating characteristic and diagnostic ions. At high collision energy (20 eV), the spectrum of Schiff base was largely uninformative, whereas both Amadori and Heyns compounds undergo characteristic fragmentations with high diagnostic value. At low collision energy values (10eV), we observed formation of prominent diagnostic ions from the Schiff base precursor, as well as extensive dehydration reactions of all three molecules. Under acidic conditions, the diagnostic fragmentation pattern of the Amadori compound featured consecutive dehydration reactions. At higher values (20 eV) it underwent the α-fission at the carbonyl group and produced a prominent diagnostic ion [AA + H + CH2]+ at m/z 88. The Schiff base was found to preferentially undergo the retro-aldol degradation and produce diagnostic ions at m/z 118 [AA + H + diose]+ and m/z 140 [AA + Na + diose]+, together with their sugar complements at m/z 85 [tetrose + H–2H2O]+ and m/z 143 [tetrose + Na]+. In the case of Heyns compound, several diagnostic ions were also detected, including the ions at m/z 154 [M + H–2H2O–C2H4O2]+, m/z 170 [AA + Na + triose]+ and m/z 142 [AA + H + Furan]+.
Analysis of Amadori compounds by high-performance cation exchange chromatography coupled to tandem mass spectrometry
Davidek, Tomas,Kraehenbuehl, Karin,Devaud, Stephanie,Robert, Fabien,Blank, Imre
, p. 140 - 147 (2007/10/03)
High-performance cation exchange chromatography coupled to tandem mass spectrometry or electrochemical detection was found to be an efficient tool for analyzing Amadori compounds derived from hexose and pentose sugars. The method allows rapid separation and identification of Amadori compounds, while benefiting from the well-known advantages of mass spectrometry, such as specificity and sensitivity. Glucose- and xylose-derived Amadori compounds of several amino acids, such as glycine, alanine, valine, leucine/isoleucine, methionine, proline, phenylalanine, and glutamic acid, were separated or discriminated using this new method. The method is suitable for the analysis of both model reaction mixtures and food products. Fructosylglutamate was found to be the major Amadori compound in dried tomatoes (～1.5 g/100 g) and fructosylproline in dried apricots (～0.2 g/100 g). Reaction of xylose and glycine at 90 °C (pH 6) for 2 h showed rapid formation of xylulosylglycine (～12 mol %, 15 min) followed by slow decrease over time. Analysis of pentose-derived Amadori compounds is shown for the first time, which represents a major breakthrough in studying occurrence, formation, and decomposition of these labile Maillard intermediates.
