Bioorganicheskaia khimiia 2000-06-01

[Hydrolysis of primary amide groups in Asn/Gln-containing peptides].

V V Onoprienko, E A Elin, A I Miroshnikov

Index: Bioorg. Khim. 26(6) , 403-10, (2000)

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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 of N-terminal amino acid residues, whereas the products of the diazomethane treatment of Boc-Asp(OMe)-Ala-OMe had a low degree of epimerization.

Related Compounds

  • Barium hydroxide m...
  • Barium hydroxide
  • Barium hydroxide o...

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