Cross-Linking of Amino Acids by Formaldehyde. Preparation and 13C NMR Spectra of Model Compounds

  • David P. Kelly
  • M. K. Dewar
  • R. B. Johns
  • Shao Wei-Let
  • J. F. Yates
Chapter
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 86A)

Abstract

Model cross-linked systems have been prepared by reacting amino acids or alkylamines with formaldehyde and various amino acid model compounds such as 2,4-dimethylphenol (tyrosine), 3-methylindole (tryptophan) and alkylamides (glutamine, asparagine. 13C NMR spectra of the products show the resonances of the formaldehyde-derived methylene carbons in the region 45-60 ppm. Interferences occur from resonances of the α-amino acid methine carbons. From the data for these products and other model compounds it has been possible to predict the shifts of the residual methylene carbons in a variety of cross-linked systems. This NMR technique shows promise as a rapid non-degradative method for identification of cross-linking sites.

Keywords

Model Compound Methylene Carbon Methine Carbon Treated Wool React Amino Acid 
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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Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

  • David P. Kelly
    • 1
  • M. K. Dewar
    • 1
  • R. B. Johns
    • 1
  • Shao Wei-Let
    • 1
  • J. F. Yates
    • 1
  1. 1.Department of Organic ChemistryUniversity of MelbourneParkvilleAustralia

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