A mechanistic study on the fragmentation of peptide‐derived Amadori products | Zendy

Stefanowicz Piotr | Zendy; Kapczynska Katarzyna | Zendy; Jaremko Mariusz | Zendy; Jaremko Łukasz | Zendy; Szewczuk Zbigniew | Zendy

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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.

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