A mechanistic study on the fragmentation of peptide-derived Amadori products

Piotr Stefanowicz*, Katarzyna Kapczynska, Mariusz Jaremko, Łukasz Jaremko, Zbigniew Szewczuk

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Gas phase fragmentation of peptide-derived Amadori products was investigated using synthetic compounds regioselectively deuterated as well as labeled with 18O at aminofructose moiety. The eliminated molecule CH2O contains exclusively protons attached to carbon C6 of the aminofructose moiety. The hydrogen atoms connected with the carbon C1 of the aminofructose moiety are partially eliminated as a component of water molecules during the dehydration process and partially dislocated within the fragmented peptide molecule. The labeled oxygen atom attached to the carbon C2 is eliminated in 100% along with the first loss of water. The MS3 experiments revealed that the product ion formed by triple dehydration of the Amadori product does not eliminate the formaldehyde molecule. On the basis of these observations we proposed a hypothetical mechanism of Amadori products' fragmentation.

Original languageEnglish (US)
Pages (from-to)1500-1508
Number of pages9
JournalJournal of Mass Spectrometry
Volume44
Issue number10
DOIs
StatePublished - Oct 2009
Externally publishedYes

Keywords

  • Amadori rearrangement
  • Glycation
  • Mechanism
  • Microwave synthesis
  • Neutral losses
  • Nonenzymatic protein modifications

ASJC Scopus subject areas

  • Spectroscopy

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