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

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

doi:10.1002/jms.1639

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 journal › Article › peer-review

15 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 language	English (US)
Pages (from-to)	1500-1508
Number of pages	9
Journal	Journal of Mass Spectrometry
Volume	44
Issue number	10
DOIs	https://doi.org/10.1002/jms.1639
State	Published - Oct 2009
Externally published	Yes

Keywords

Amadori rearrangement
Glycation
Mechanism
Microwave synthesis
Neutral losses
Nonenzymatic protein modifications

ASJC Scopus subject areas

Spectroscopy

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10.1002/jms.1639

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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.",

keywords = "Amadori rearrangement, Glycation, Mechanism, Microwave synthesis, Neutral losses, Nonenzymatic protein modifications",

author = "Piotr Stefanowicz and Katarzyna Kapczynska and Mariusz Jaremko and {\L}ukasz Jaremko and Zbigniew Szewczuk",

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AU - Stefanowicz, Piotr

AU - Kapczynska, Katarzyna

AU - Jaremko, Mariusz

AU - Jaremko, Łukasz

AU - Szewczuk, Zbigniew

PY - 2009/10

Y1 - 2009/10

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AB - 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.

KW - Amadori rearrangement

KW - Glycation

KW - Mechanism

KW - Microwave synthesis

KW - Neutral losses

KW - Nonenzymatic protein modifications

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

Abstract

Keywords

ASJC Scopus subject areas

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