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Application of liquid chromatography-tandem mass spectrometry for the characterization of galactosylated and tagatosylated beta-lactoglobulin peptides derived from in vitro gastrointestinal digestion.
J Chromatogr A. 2009 Oct 23; 1216(43):7205-12.JC

Abstract

This article describes a comprehensive characterization of bovine beta-lactoglobulin peptides glycated with an aldohexose (galactose) or a ketohexose (tagatose), derived from in vitro gastrointestinal digestion, by liquid chromatography coupled to positive electrospray ion trap tandem mass spectrometry. In addition to the dissociation pathway previously described for aldohexoses-derived Amadori compounds, i.e. formation of the pyrylium ([M+H](+)-54) and furylium ions ([M+H](+)-84) via the oxonium ion ([M+H](+)-18), another and more direct fragmentation route involving the formation of the imminium ion ([M+H](+)-150) is also reported following extensive glycation rates of beta-lactoglobulin with both carbohydrates. These results indicated that the analysis of digested proteins by LC-ESI-MS(2) on a three-dimensional ion trap monitoring neutral losses is an efficient and direct method to identify peptides glycated not only through the Amadori rearrangement but also via the Heyns rearrangement. Nevertheless, as the predominating MS(2) fragmentation pattern of the glycated peptides is derived from the sugar moiety, the sequence-informative b- and y-ions resulting from peptide backbone cleavage were undetected. To overcome this drawback, and taking advantage of multi-stage fragmentation capabilities of ion traps, the indicative Amadori and Heyns-derived imminium ions were successfully used in MS(3) analyses to identify the peptide backbone, as well as the specific glycation site. In addition, further MS(4) analyses were needed to carry out the characterization of doubly glycated peptides.

Authors+Show Affiliations

Instituto de Fermentaciones Industriales (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.No 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

19747681

Citation

Corzo-Martínez, Marta, et al. "Application of Liquid Chromatography-tandem Mass Spectrometry for the Characterization of Galactosylated and Tagatosylated Beta-lactoglobulin Peptides Derived From in Vitro Gastrointestinal Digestion." Journal of Chromatography. A, vol. 1216, no. 43, 2009, pp. 7205-12.
Corzo-Martínez M, Lebrón-Aguilar R, Villamiel M, et al. Application of liquid chromatography-tandem mass spectrometry for the characterization of galactosylated and tagatosylated beta-lactoglobulin peptides derived from in vitro gastrointestinal digestion. J Chromatogr A. 2009;1216(43):7205-12.
Corzo-Martínez, M., Lebrón-Aguilar, R., Villamiel, M., Quintanilla-López, J. E., & Moreno, F. J. (2009). Application of liquid chromatography-tandem mass spectrometry for the characterization of galactosylated and tagatosylated beta-lactoglobulin peptides derived from in vitro gastrointestinal digestion. Journal of Chromatography. A, 1216(43), 7205-12. https://doi.org/10.1016/j.chroma.2009.08.054
Corzo-Martínez M, et al. Application of Liquid Chromatography-tandem Mass Spectrometry for the Characterization of Galactosylated and Tagatosylated Beta-lactoglobulin Peptides Derived From in Vitro Gastrointestinal Digestion. J Chromatogr A. 2009 Oct 23;1216(43):7205-12. PubMed PMID: 19747681.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Application of liquid chromatography-tandem mass spectrometry for the characterization of galactosylated and tagatosylated beta-lactoglobulin peptides derived from in vitro gastrointestinal digestion. AU - Corzo-Martínez,Marta, AU - Lebrón-Aguilar,Rosa, AU - Villamiel,Mar, AU - Quintanilla-López,Jesús Eduardo, AU - Moreno,F Javier, Y1 - 2009/08/26/ PY - 2009/04/17/received PY - 2009/06/24/revised PY - 2009/08/24/accepted PY - 2009/9/15/entrez PY - 2009/9/15/pubmed PY - 2010/1/16/medline SP - 7205 EP - 12 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1216 IS - 43 N2 - This article describes a comprehensive characterization of bovine beta-lactoglobulin peptides glycated with an aldohexose (galactose) or a ketohexose (tagatose), derived from in vitro gastrointestinal digestion, by liquid chromatography coupled to positive electrospray ion trap tandem mass spectrometry. In addition to the dissociation pathway previously described for aldohexoses-derived Amadori compounds, i.e. formation of the pyrylium ([M+H](+)-54) and furylium ions ([M+H](+)-84) via the oxonium ion ([M+H](+)-18), another and more direct fragmentation route involving the formation of the imminium ion ([M+H](+)-150) is also reported following extensive glycation rates of beta-lactoglobulin with both carbohydrates. These results indicated that the analysis of digested proteins by LC-ESI-MS(2) on a three-dimensional ion trap monitoring neutral losses is an efficient and direct method to identify peptides glycated not only through the Amadori rearrangement but also via the Heyns rearrangement. Nevertheless, as the predominating MS(2) fragmentation pattern of the glycated peptides is derived from the sugar moiety, the sequence-informative b- and y-ions resulting from peptide backbone cleavage were undetected. To overcome this drawback, and taking advantage of multi-stage fragmentation capabilities of ion traps, the indicative Amadori and Heyns-derived imminium ions were successfully used in MS(3) analyses to identify the peptide backbone, as well as the specific glycation site. In addition, further MS(4) analyses were needed to carry out the characterization of doubly glycated peptides. SN - 1873-3778 UR - https://www.unboundmedicine.com/medline/citation/19747681/Application_of_liquid_chromatography_tandem_mass_spectrometry_for_the_characterization_of_galactosylated_and_tagatosylated_beta_lactoglobulin_peptides_derived_from_in_vitro_gastrointestinal_digestion_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(09)01260-6 DB - PRIME DP - Unbound Medicine ER -