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Reactions of Proteins with Dehydroalanines

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

Abstract

Reactions of proteins with dehydroalanine or derivatives of dehydroalanine were studied as models for protein crosslinking. Treatment of casein, bovine serum albumin, lysozyme, wool or polylysine with acetamido- and phenylacetamido acrylic acid methyl esters at pH 9–10 converted varying amounts of lysine to lysinoalanine residues. However, complete transformation was not achieved. Incomplete reaction is attributed to partial hydrolysis of the esters to the less reactive acrylic acids under the reaction conditions. Similar studies were made of the reactivities of protein SH groups generated by reduction of disulfide bonds by tributylphosphine. The SH groups could be completely alkylated at pH 7. 6 in aqueous propanol, as shown by nearly quantitative recovery of lanthionine. Such a procedure might therefore be used to estimate cystine contents of proteins.

Keywords

Hydrolysis DMSO Cysteine Lysine Methionine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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Copyright information

© Springer Science+Business Media New York 1977

Authors and Affiliations

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

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