Linked Life Data

11400213

Source:http://linkedlifedata.com/resource/pubmed/id/11400213

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
12
pubmed:dateCreated
2001-6-11
pubmed:abstractText
Glucose-substituted imidazolidinones related to the endogenous opioid peptide leucine-enkephalin have been investigated using fast atom bombardment tandem mass spectrometry (FAB-MS/MS) and electrospray ionization tandem mass spectrometry (ESI-MS/MS). In addition to Amadori compounds, the studied imidazolidinones represent a novel type of the early glycation products formed in the Maillard reaction. To obtain insight into the fragmentation behavior of these carbohydrate-peptide adducts, we also studied synthetic precursors of the glucose-substituted imidazolidinones as well as the corresponding isopropylidene derivatives. The collision-induced dissociation (CID) spectra of [M + H](+) ions of all these imidazolidinones have been compared. Detailed analysis showed that fragmentation of each compound generates two ions at m/z 566 and m/z 598 which are characteristic and undoubtedly confirm the imidazolidinone-type structure. These two significant ions were identified as the M + 10 and M + 42 modifications of the N-terminus of the parent opioid pentapeptide effected by the carbohydrate moiety. Furthermore, the ion at m/z 178 is identified as the M + 42 modification of the immonium ion of the N-terminal amino acid (tyrosine) also effected by the carbohydrate moiety. They can be used as diagnostic ions for imidazolidinone-type compounds in studying the Maillard reaction. Thus, we have demonstrated the utility of FAB-MS/MS and ESI-MS/MS in the structural determination and identification of such novel peptide-carbohydrate adducts, useful in understanding the details of the mechanism of non-enzymatic glycation in vivo.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:issn
0951-4198
pubmed:author
pubmed:copyrightInfo
Copyright 2001 John Wiley & Sons, Ltd.
pubmed:issnType
Print
pubmed:volume
15
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1022-9
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
2001
pubmed:articleTitle
The early glycation products of the Maillard reaction: mass spectrometric characterization of novel imidazolidinones derived from an opioid pentapeptide and glucose.
pubmed:affiliation
Department of Organic Chemistry and Biochemistry, Ruder Boskovi? Institute, PO Box 180, 10002 Zagreb, Croatia. roscic@rudjer.irb.hr
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't