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The early glycation products of the Maillard reaction: mass spectrometric characterization of novel imidazolidinones derived from an opioid pentapeptide and glucose.
Rapid Commun Mass Spectrom. 2001; 15(12):1022-9.RC

Abstract

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.

Authors+Show Affiliations

Department of Organic Chemistry and Biochemistry, Ruder Bosković Institute, PO Box 180, 10002 Zagreb, Croatia. roscic@rudjer.irb.hrNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

11400213

Citation

Roscić, M, et al. "The Early Glycation Products of the Maillard Reaction: Mass Spectrometric Characterization of Novel Imidazolidinones Derived From an Opioid Pentapeptide and Glucose." Rapid Communications in Mass Spectrometry : RCM, vol. 15, no. 12, 2001, pp. 1022-9.
Roscić M, Versluis C, Kleinnijenhuis AJ, et al. The early glycation products of the Maillard reaction: mass spectrometric characterization of novel imidazolidinones derived from an opioid pentapeptide and glucose. Rapid Commun Mass Spectrom. 2001;15(12):1022-9.
Roscić, M., Versluis, C., Kleinnijenhuis, A. J., Horvat, S., & Heck, A. J. (2001). The early glycation products of the Maillard reaction: mass spectrometric characterization of novel imidazolidinones derived from an opioid pentapeptide and glucose. Rapid Communications in Mass Spectrometry : RCM, 15(12), 1022-9.
Roscić M, et al. The Early Glycation Products of the Maillard Reaction: Mass Spectrometric Characterization of Novel Imidazolidinones Derived From an Opioid Pentapeptide and Glucose. Rapid Commun Mass Spectrom. 2001;15(12):1022-9. PubMed PMID: 11400213.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The early glycation products of the Maillard reaction: mass spectrometric characterization of novel imidazolidinones derived from an opioid pentapeptide and glucose. AU - Roscić,M, AU - Versluis,C, AU - Kleinnijenhuis,A J, AU - Horvat,S, AU - Heck,A J, PY - 2001/6/16/pubmed PY - 2001/7/28/medline PY - 2001/6/16/entrez SP - 1022 EP - 9 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 15 IS - 12 N2 - 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. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/11400213/The_early_glycation_products_of_the_Maillard_reaction:_mass_spectrometric_characterization_of_novel_imidazolidinones_derived_from_an_opioid_pentapeptide_and_glucose_ L2 - https://doi.org/10.1002/rcm.334 DB - PRIME DP - Unbound Medicine ER -