Further Studies of the Chemical Cleavage of the Tryptophyl Bond by Ozonization-hydrazine Treatment

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概要

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• The second step (hydrazine treatment) in the chemical cleavage of the tryptophyl bond according to the scheme proposed previously was further studied under mild conditions using a model <I>N</I>′-formylkynurenyl peptide, carbobenzoxy-L-alanyl-<I>N</I>′-formyl-L-kynurenyl-L-leucine. The reaction of the model compound with an excess of hydrazine acetate at 25–30°C for 24–48 hr gave rise to the selective cleavage of the kynurenyl bond together with a concomitant tetrahydropyridazone formation. The maximum cleavage was 80–90%. It was then suggested that the incomplete cleavage of the tryptophyl bond in synthetic oligopeptides by means of ozonizationhydrazine treatment was mainly due to insufficient conversion of the indole nucleus into <I>N</I>′-formylanthranyl grouping in the first step (ozonization).

• 公益社団法人 日本化学会の論文

著者

• Sakiyama Fumio

  Institute For Protein Research Osaka University

• Sakai Shin-ichiro

  Institute Of Space And Astronautical Science Japan Aerospace Exploration Agency

• SAKIYAMA Fumio

  Institute for Protein Research, Osaka University

• Sakai Shin-ichiro

  Institute for Protein Research, Osaka University

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