Document Detail

Fragmentation behavior of glycated peptides derived from D-glucose, D-fructose and D-ribose in tandem mass spectrometry.
MedLine Citation:
PMID:  17063450     Owner:  NLM     Status:  MEDLINE    
Nonenzymatic glycosylation (or glycation) is a common nonenzymatic side-chain specific sequence-independent posttranslational modification formed by the reaction of reducing carbohydrates with free amino groups. Thus, proteins can react with aldoses or ketoses to yield Amadori or Heynes compounds, respectively. Here, the fragmentation behavior of D-glucose and D-ribose-derived Amadori peptides as well as D-fructose-derived Heynes peptides were studied by collision-induced fragmentation (CID) after electrospray (ESI) or matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS). All three sugar moieties displayed characteristic fragmentation patterns accompanying the parent and the fragment ions, which could be explained by consecutive losses of water and formaldehyde. Glucose-derived Amadori parent and fragment ions displayed losses of 18, 36, 54, 72, and 84 u at a characteristic intensity distribution compared with losses of 18, 36, 54, 72, 84, and 96 u for D-fructose-derived ions and losses of 18, 36, and 54 u for ribose-derived ions. Furthermore, each sugar moiety produced indicative lysine-derived immonium ions that were successfully used in a precursor ion scan analysis to identify Amadori peptides in a tryptic digest of bovine serum albumin (BSA) glycated with D-glucose. BSA was modified on lysine residues at positions 36, 160, 235, 256, 401, and 548.
Andrej Frolov; Peter Hoffmann; Ralf Hoffmann
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of mass spectrometry : JMS     Volume:  41     ISSN:  1076-5174     ISO Abbreviation:  J Mass Spectrom     Publication Date:  2006 Nov 
Date Detail:
Created Date:  2006-11-20     Completed Date:  2007-05-15     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9504818     Medline TA:  J Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  1459-69     Citation Subset:  IM    
Copyright Information:
Copyright 2006 John Wiley & Sons, Ltd.
Bioanalytics, Center for Biotechnology and Biomedicine, Faculty of Chemistry and Mineralogy, University of Leipzig, Deutscher Platz 5, 04103 Leipzig, Germany.
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MeSH Terms
Amino Acid Sequence
Fructose / chemistry*
Glucose / chemistry*
Models, Molecular
Molecular Sequence Data
Molecular Structure
Peptides / chemistry*
Ribose / chemistry*
Serum Albumin
Spectrometry, Mass, Electrospray Ionization
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Tandem Mass Spectrometry
Reg. No./Substance:
0/Peptides; 0/Serum Albumin; 30237-26-4/Fructose; 50-69-1/Ribose; 50-99-7/Glucose

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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