New Amino Acid Derivatives Formed by Alkaline Treatment of Proteins

  • John W. Finley
  • Mendel Friedman
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 86)


Intense heat treatment of proteins at high pH favors formation of transient, reactive intermediates derived from serine and cystine. The postulated dehydroalanine intermediate reacts further with the ε-amino groups side chains and sulfhydryl groups of cysteine residues to form derivatives of lysinoalanine and lanthionine. Recent studies indicate that besides these crosslinked products, several others are formed, by reaction of histidine, arginine, and possibly other residues. For this reason, caution should be exercised in assigning the prelysine peak(s) of an amino acid chromatogram to lysinoalanine. These results suggest that unnatural amino acid derivatives, other than lysinoalanine, may also contribute to the toxic effects reported from studies in which alkali-treated protein was fed to rats.


Hydrolysis Serine Lysine Arginine Alanine 
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Copyright information

© Springer Science+Business Media New York 1977

Authors and Affiliations

  • John W. Finley
    • 1
  • Mendel Friedman
    • 1
  1. 1.Western Regional Research Laboratory, Agricultural Research ServiceU.S. Department of AgricultureBerkeleyUSA

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