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Novel acyclic amide-conjugated nucleosides and their analogues.

Authors
  • Boncel, Slawomir1
  • Walczak, Krzysztof
  • 1 Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Gliwice, Poland. [email protected] , (Poland)
Type
Published Article
Journal
Nucleosides, nucleotides & nucleic acids
Publication Date
Feb 01, 2009
Volume
28
Issue
2
Pages
103–117
Identifiers
DOI: 10.1080/15257770902736467
PMID: 19219740
Source
Medline
License
Unknown

Abstract

An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.

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