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Reactivity of Maillard products with a pyrrole structure

Untersuchungen zur Reaktivität von Maülard-Produkten mit Pyrrol-Struktur

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Zusammenfassung

Bei der Maillard-Reaktion werden neben anderen Produkten Pyrrole mit Hydroxyalkyl-Seitenketten gebildet. Vermutlich sind derartige Substanzen an der Quervernetzung von Proteinen sowie an der Bildung polymerer, brauner Produkte beteiligt. Untersuchungen mit Modellverbindungen zeigten, daß Hydroxylgruppen in α-Stellung zum Pyrrol leicht durch Mercaptane, Alkohole und Sulfit, jedoch weniger leicht durch Amine substituiert werden. Eine Quervernetzung von Proteinen könnte danach über Lysin- und Cysteinreste erfolgen.

Summary

During the course of the Maillard reaction several pyrroles with hydroxyalkyl side-chains are formed together with other products. These substances are supposed to be responsible for cross-linking of proteins and polymerisation, forming brown products. Investigation of model compounds revealed that hydroxy groups in the α-position of a pyrrole are easily substituted by mercaptanes, alcohols and sulphite but less readily by amines. According to these results cross-linking of proteins may occur by connection of lysine and cystein residues through a pyrrole moiety.

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Authors and Affiliations

  1. Institut für Lebensmittelchemie und Analytische Chemie der Universität Stuttgart, Pfaffenwaldring 55, W-7000, Stuttgart 80, Germany

    E. Klein & F. Ledl

  2. Institut für Pharmazie und Lebensmittelchemie der Universität München, Sophienstrasse 10, W-8000, München 2, Germany

    W. Bergmüller & T. Severin

Authors
  1. E. Klein
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  2. F. Ledl
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  3. W. Bergmüller
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  4. T. Severin
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Klein, E., Ledl, F., Bergmüller, W. et al. Reactivity of Maillard products with a pyrrole structure. Z Lebensm Unters Forch 194, 556–560 (1992). https://doi.org/10.1007/BF01185483

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  • DOI: https://doi.org/10.1007/BF01185483

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