Characterizing lysinoalanine crosslinks in food systems: Discovery of a diagnostic ion in model peptides using MALDI mass spectrometry

Aebersold, 2003, Mass spectrometry-based proteomics [Review], Nature, 422, 198, 10.1038/nature01511 Boschin, 2003, Lysinoalanine content of formulas for enteral nutrition [Article], Journal of Dairy Science, 86, 2283, 10.3168/jds.S0022-0302(03)73820-X Cartus, 2017, D-Amino acids and cross-linked amino acids in food, 251 Courcelles, 2017, CLMSVault: A software suite for protein cross-linking mass-spectrometry data analysis and visualization [Article], Journal of Proteome Research, 16, 2645, 10.1021/acs.jproteome.7b00205 D'Agostina, 2003, Updating on the lysinoalanine content of commercial infant formulae and beicost products [Article], Food Chemistry, 80, 483, 10.1016/S0308-8146(02)00316-3 Dyer, 2013, Redox proteomic evaluation of bleaching and alkali damage in human hair [Article], International Journal of Cosmetic Science, 35, 555, 10.1111/ics.12076 Friedman, 1999, Chemistry, biochemistry, nutrition, and microbiology of lysinoalanine, lanthionine, and histidinoalanine in food and other proteins [Review], Journal of Agricultural and Food Chemistry, 47, 1295, 10.1021/jf981000+ Friedman, 2008, Alkali and/or acid treatment: Dietary significance of processing-induced lysinoalanine in food, 473 Friedman, 1982, The nutritional value of lysinoalanine as a source of lysine for mice [Article], Nutrition Reports International, 26, 937 Friedman, 1984, Factors governing lysinoalanine formation in soy proteins [Article], Journal of Food Science, 49, 1282, 10.1111/j.1365-2621.1984.tb14970.x Fritsch, 1981, Improved method for determination of lysinoalanine in food [Article], Zeitschrift für Lebensmittel-Untersuchung und -Forschung (Journal of Food Inspection and Research), 172, 435, 10.1007/BF01415852 Fujimoto, 1984, Age variation in histidinoalanine cross-links in proteoglycan subunits from human articular cartilage [Article], Topics in Catalysis, 4, 395 Gao, 2006, Pro-CrossLink. Software tool for protein cross-linking and mass spectrometry [Article], Analytical Chemistry, 78, 2145, 10.1021/ac051339c Gerrard, 2002, Protein-protein crosslinking in food: Methods, consequences, applications [Article], Trends in Food Science and Technology, 13, 391, 10.1016/S0924-2244(02)00257-1 Goyder, 2013, Strategies in mass spectrometry for the assignment of cys-cys disulfide connectivities in proteins [Review], Expert Review of Proteomics, 10, 489, 10.1586/14789450.2013.837663 Hasegawa, 1982, Gas chromatography-mass spectrometry of lysinoalanine and the related crosslinked amino acids in alkali-treated food proteins [Article], Agricultural and Biological Chemistry, 46, 2513 Hasegawa, 1987, Determination of the lysinoalanine content in commercial foods by gas chromatography-selected ion monitoring [Article], Agricultural and Biological Chemistry, 51, 2889 Kume, 1984, Effect of gamma-irradiation on lysinoalanine in various feedstuffs and model systems [Article], Journal of Agricultural and Food Chemistry, 32, 656, 10.1021/jf00123a057 Lassé, 2015, The impact of pH, salt concentration and heat on digestibility and amino acid modification in egg white protein [Article], Journal of Food Composition and Analysis, 38, 42, 10.1016/j.jfca.2014.08.007 Lebendiker, 2014, Production of prone-to-aggregate proteins [Review], FEBS Letters, 588, 236, 10.1016/j.febslet.2013.10.044 Leitner, 2012, Expanding the chemical cross-linking toolbox by the use of multiple proteases and enrichment by size exclusion chromatography [Article], Molecular and Cellular Proteomics, 11, 10.1074/mcp.M111.014126 Leitner, 2014, Lysine-specific chemical cross-linking of protein complexes and identification of cross-linking sites using LC-MS/MS and the xQuest/xProphet software pipeline [Article], Nature Protocols, 9, 120, 10.1038/nprot.2013.168 Maes, 2017, Protein-protein cross-linking and human health: The challenge of elucidating with mass spectrometry [Review], Expert Review of Proteomics, 14, 917, 10.1080/14789450.2017.1362336 Maiolica, 2007, Structural analysis of multiprotein complexes by cross-linking, mass spectrometry, and database searching [Article], Molecular and Cellular Proteomics, 6, 2200, 10.1074/mcp.M700274-MCP200 McKerchar, 2019, Protein-protein crosslinking in food: Proteomic characterisation methods, consequences and applications [Review], Trends in Food Science and Technology, 86, 217, 10.1016/j.tifs.2019.02.005 Monahan, 1995, Effect of pH and temperature on protein unfolding and thiol/ disulfide interchange reactions during heat-induced gelation of whey proteins [Article], Journal of Agricultural and Food Chemistry, 43, 46, 10.1021/jf00049a010 Nashef, 1977, Effects of alkali on proteins. Disulfides and their products [Article], Journal of Agricultural and Food Chemistry, 25, 245, 10.1021/jf60210a020 Onwulata, 2006, Properties of whey protein isolates extruded under acidic and alkaline conditions [Article], Journal of Dairy Science, 89, 71, 10.3168/jds.S0022-0302(06)72070-7 Pellegrino, 2010, Detection of milk powder and caseinates in Halloumi cheese [Article], Journal of Dairy Science, 93, 3453, 10.3168/jds.2009-2923 Pellegrino, 1996, Sensitive determination of lysinoalanine for distinguishing natural from imitation mozzarella cheese [Article], Journal of Dairy Science, 79, 725, 10.3168/jds.S0022-0302(96)76419-6 Possompes, 1986, Effect of severely alkali-treated casein on gastrointestinal transit and selected intestinal enzyme activities [Article], Advances in Experimental Medicine and Biology, 199, 517, 10.1007/978-1-4757-0022-0_30 Rappsilber, 2011, The beginning of a beautiful friendship: Cross-linking/mass spectrometry and modelling of proteins and multi-protein complexes [Article], Journal of Structural Biology, 173, 530, 10.1016/j.jsb.2010.10.014 Riffle, 2016, ProXL (protein cross-linking database): A platform for analysis, visualization, and sharing of protein cross-linking mass spectrometry data [Article], Journal of Proteome Research, 15, 2863, 10.1021/acs.jproteome.6b00274 Rinner, 2008, Identification of cross-linked peptides from large sequence databases [Article], Nature Methods, 5, 315, 10.1038/nmeth.1192 Rombouts, 2012, Heat-induced cross-linking and degradation of wheat gluten, serum albumin, and mixtures thereof [Article], Journal of Agricultural and Food Chemistry, 60, 10133, 10.1021/jf3024672 Rombouts, 2016, Identification of lanthionine and lysinoalanine in heat-treated wheat gliadin and bovine serum albumin using tandem mass spectrometry with higher-energy collisional dissociation [Article], Amino Acids, 48, 959, 10.1007/s00726-015-2139-2 Sternberg, M., & Kim, C. Y. (1977). Lysinoalanine formation in protein food ingredients. In M. Friedman (Ed.), Protein crosslinking: Nutritional and medical consequences (1 ed., pp. 73-84). Springer US. https://doi.org/10.1007/978-1-4757-9113-6_5. Wang, 2008, MALDI MS sample preparation by using paraffin wax film: Systematic study and application for peptide analysis [Article], Analytical Chemistry, 80, 491, 10.1021/ac701614f Wilkins, 1997, Detailed peptide characterization using PEPTIDEMASS - A World-Wide-Web-accessible tool [Conference Paper], Electrophoresis, 18, 403, 10.1002/elps.1150180314 Yugandhar, 2020, MaxLinker: Proteome-wide cross-link identifications with high specificity and sensitivity [Article], Molecular and Cellular Proteomics, 19, 554, 10.1074/mcp.TIR119.001847 Zhao, 2016, Formation of lysinoalanine in egg white under alkali treatment [Article], Poultry Science, 95, 660, 10.3382/ps/pev372