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Synthesis 2012(7): 1011-1025  
DOI: 10.1055/s-0031-1289737
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Incorporation into Oligodeoxynucleotides of Carbocyclic exo-Amino Nucleosides

Oezlem Yaren, Pascal Röthlisberger, Christian J. Leumann*
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland
Fax: +41(31)6313422; e-Mail: leumann@ioc.unibe.ch;
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Publication History

Received 23 December 2011
Publication Date:
02 March 2012 (online)

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Abstract

The preparation of a series of carbocyclic exo-amino nucleosides from selected primary aromatic amines in both the C1′ α- and β-epimeric form as well as the corresponding building blocks for DNA synthesis is described. These nucleosides were incorporated into oligodeoxynucleotides and their base-pairing properties with natural bases and, in part, with themselves investigated. The results obtained confirm that such nucleoside analogues engage in specific interactions with natural nucleotides in DNA duplexes. In addition they can form self-pairs that match or exceed the stability of Watson-Crick base-pairs. Thus, carbocyclic exo-amino nucleosides can be taken into consideration in the design of novel base-pairs for the extension of the genetic alphabet, or for other applications in biotechnology.

1 Introduction

2 Synthetic Routes

2.1 Synthesis of Carbocyclic exo-Amino Nucleosides and Building Blocks

2.2 Synthesis of Oligonucleotides

3 Pairing Properties of Oligonucleotides

4 Discussion and Conclusions

Key words

nucleosides - oligonucleotides - nucleobases - molecular recognition - medicinal chemistry

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