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

✍ Scribed by Piotr Stefanowicz; Katarzyna Kapczynska; Mariusz Jaremko; Łukasz Jaremko; Zbigniew Szewczuk

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
356 KB
Volume
44
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

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.

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