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Identification of lanthionine and lysinoalanine in heat-treated wheat gliadin and bovine serum albumin using tandem mass spectrometry with higher-energy collisional dissociation

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Abstract

The present manuscript reports on the identification of various dehydroamino acid-derived bonds and cross-links resulting from thermal treatment (excess water, 240 min, 130 °C) of two model food proteins, bovine serum albumin, and wheat gliadin. S-Carbamidomethylated tryptic and chymotryptic digests of unheated (control) and heated serum albumin and gliadin, respectively, were analyzed by liquid chromatography coupled to tandem mass spectrometry (LC–ESI–MS/MS) with higher-energy collisional dissociation (HCD). Heat-induced β-elimination of cystine, serine and threonine, and subsequent Michael addition of cysteine and lysine to dehydroalanine and 3-methyl-dehydroalanine were demonstrated. Lanthionine, lysinoalanine, 3-methyl-lanthionine, and 3-methyl-lysinoalanine were identified. The detection of inter-chain lanthionine in both bovine serum albumin and wheat gliadin suggests the significance of these cross-links for food texture.

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Acknowledgments

This work is part of the Methusalem programme “Food for the future” at the KU Leuven. I. Rombouts wishes to acknowledge the Research Foundation-Flanders (FWO, Brussels, Belgium) for a function as postdoctoral researcher. W. Vermaelen is gratefully thanked for his technical assistance. J. A. Delcour is W. K. Kellogg Chair in Cereal Science and Nutrition at the KU Leuven.

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Authors and Affiliations

  1. Laboratory of Food Chemistry and Biochemistry and Leuven Food Science and Nutrition Research Centre (LFoRCe), KU Leuven, Kasteelpark Arenberg 20, Box 2463, 3001, Leuven, Belgium

    Ine Rombouts, Marlies A. Lambrecht & Jan A. Delcour

  2. Laboratory for Tropical Crop Improvement, KU Leuven, Willem de Croylaan 42, Box 2455, 3001, Leuven, Belgium

    Sebastien C. Carpentier

  3. Facility for SYstems BIOlogy Based MAss Spectrometry, Herestraat 49, 3000, Leuven, Belgium

    Sebastien C. Carpentier

Authors
  1. Ine Rombouts
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  2. Marlies A. Lambrecht
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  3. Sebastien C. Carpentier
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  4. Jan A. Delcour
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Correspondence to Ine Rombouts.

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Rombouts, I., Lambrecht, M.A., Carpentier, S.C. et al. Identification of lanthionine and lysinoalanine in heat-treated wheat gliadin and bovine serum albumin using tandem mass spectrometry with higher-energy collisional dissociation. Amino Acids 48, 959–971 (2016). https://doi.org/10.1007/s00726-015-2139-2

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  • DOI: https://doi.org/10.1007/s00726-015-2139-2

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