Russian Journal of Bioorganic Chemistry

, Volume 26, Issue 6, pp 361–368 | Cite as

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

  • V. V. Onoprienko
  • E. A. Yelin
  • A. I. Miroshnikov


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.

Key words

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


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Copyright information

© MAIK “Nauka/Interperiodica” 2000

Authors and Affiliations

  • V. V. Onoprienko
    • 1
  • E. A. Yelin
    • 1
  • A. I. Miroshnikov
    • 1
  1. 1.Shemyakin-Ovchinnikov Institute of Bioorganic ChemistryRussian Academy of SciencesGSP-7 MoscowRussia

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