Efficient approach for producing pseudopeptide fragments – the key intermediates of the synthesis of polyamide nucleic acid mimics (PANAM)

The convenient synthesis of the key structure fragments of polyamide nucleic acid mimic (PANAM) monomers according to route using Mitsunobu’s reaction and subsequent thiolysis of protective o-nitrobenzenesulphonyl group is presented. The purification of target secondary amines was occurred after the thiolysis stage by an extraction at various pH, without isolation of fully protected pseudopeptide intermediate derivatives. Thus, it were obtained BocGlyΨAlaOAll, BocAlaΨGlyOMe, BocGluΨGlyOAll, BocGlyΨGlyOMe, CbzAlaΨGlyOMe, CbzGlu(Ot Bu)ΨGlyOMe. It was shown that yields of target compounds are comparable both by the employing of purification stage of intermediates and without it. The key condition of successful applying of presented method is the absence of initial “acid component” in the reaction mixture undertaken to thiolysis.

pseudopeptides, nucleic acid mimics, Mitsunobu’s reaction.

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