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

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Abstract

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.

About the Authors

A. V. Dezhenkov
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


I. A. Prokhorov
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


A. I. Lyutik
Московский государственный университет тонких химических технологий им. М.В. Ломоносова
Russian Federation


V. I. Shvets
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


Yu. G. Kirillova Yu.G.
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


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For citation:


Dezhenkov A.V., Prokhorov I.A., Lyutik A.I., Shvets V.I., Kirillova Yu.G. Yu.G. Efficient approach for producing pseudopeptide fragments – the key intermediates of the synthesis of polyamide nucleic acid mimics (PANAM). Fine Chemical Technologies. 2013;8(6):108-110. (In Russ.)

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ISSN 2410-6593 (Print)
ISSN 2686-7575 (Online)