The Non-enzymatic Cleavage of Peptide Bonds. II. The Chemical Cleavage of the Tryptophyl Bond in Several Synthetic Peptides

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概要

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• Several synthetic peptide derivatives containing tryptophan were examined for the selective cleavage at the tryptophyl residue, according to a new scheme involving ozonization and subsequent treatment with hydrazine. The ozonization reaction of the tryptophyl residue was carried out in the presence and in the absence of resorcinol in formic acid. Then the reaction of the ozonized product with hydrazine was performed at pH 3.6 to bring about the tryptophyl bond cleavage. The yield of the present cleavage reaction ranged from 35 to 68% on the basis of the starting peptide derivative used. The cleavage reaction could be followed spectroscopically in parallel with the exposure of the amino group acylated by the tryptophyl residue. The 2,3,4,5-tetrahydropyridazone derivative derived from the parental tryptophyl residue was identified by a comparison of both its chromato-graphic behavior and its ultraviolet spectrum with those of the standard sample. Thus it was confirmed that the present cleavage proceeded through the proposed reaction sequence.

• 公益社団法人 日本化学会の論文

著者

• Sakiyama Fumio

  Institute For Protein Research Osaka University

• SAKIYAMA Fumio

  Institute for Protein Research, Osaka University

• Morishita Michiyo

  Institute for Protein Research, Osaka University

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• The Non-enzymatic Cleavage of Peptide Bonds. II. The Chemical Cleavage of the Tryptophyl Bond in Several Synthetic Peptides

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