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The hydrolysis of primary amide groups in Asn/Gln-containing peptides

Abstract

Peptides Boc-Ala-Asn/Gln-OH and Boc-Asn/Gln-Ala-OH were saponified with barium hydroxide to corresponding Asp/Glu-containing peptides. Under the conditions of saponification, Boc-Asn-Ala-OH additionally afforded Boc-Asp-OH, isopeptide Boc-Asp(Ala)-OH, and Boc-NHSuc>Ala-OH, with the third being the key intermediate in these transformations. Boc-Asp(OMe)-Ala-OMe underwent similar transformations under treatment with diazomethane or triethylamine. Saponification with barium hydroxide was accompanied by a high epimerization ofN-terminal amino acid residues, whereas the products of the diazomethane treatment of Boc-Asp(OMe)-Ala-OMe had a low degree of epimerization.

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Correspondence to V. V. Onoprienko.

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Onoprienko, V.V., Yelin, E.A. & Miroshnikov, A.I. The hydrolysis of primary amide groups in Asn/Gln-containing peptides. Russ J Bioorg Chem 26, 361–368 (2000). https://doi.org/10.1007/BF02758662

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  • DOI: https://doi.org/10.1007/BF02758662

Key words

  • asparagine
  • aspartic acid
  • glutamine
  • glutamic acid
  • peptides
  • epimerization
  • rearrangement
  • primary amides
  • selective saponification