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A mechanistic study on the fragmentation of peptide‐derived Amadori products
Author(s) -
Stefanowicz Piotr,
Kapczynska Katarzyna,
Jaremko Mariusz,
Jaremko Łukasz,
Szewczuk Zbigniew
Publication year - 2009
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1639
Subject(s) - chemistry , amadori rearrangement , moiety , molecule , fragmentation (computing) , peptide , deuterium , hydrogen atom , stereochemistry , organic chemistry , glycation , biochemistry , physics , receptor , alkyl , quantum mechanics , computer science , operating system
Gas phase fragmentation of peptide‐derived Amadori products was investigated using synthetic compounds regioselectively deuterated as well as labeled with 18 O at aminofructose moiety. The eliminated molecule CH 2 O 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 MS 3 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. Copyright © 2009 John Wiley & Sons, Ltd.