PMID: 9545434May 23, 1998Paper

Bicyclo[3.2.1]-DNA, a new DNA analog with a rigid backbone and flexibly linked bases: pairing properties with complementary DNA

Chemistry & Biology
C Epple, C J Leumann

Abstract

The structural and conformational variety in nucleic acid complexes is largely controlled by the sugar-phosphate backbone. In order to modulate specific features such as strength or selectivity of complex formation by designing nucleotide analogs, a deeper understanding of the relationship between mononucleotide structures and the properties of their oligomers is necessary. One approach involves comparing the properties of DNA analogs displaying well defined modifications in their backbone structure with those of natural DNA and RNA. We have designed and synthesized a new DNA analog, 'bicyclo[3.2.1]-DNA', which has a rigid phosphodiester backbone that emulates a B-DNA-type conformation, to which the nucleobases are attached via a flexible open-chain linker. A UV-melting curve analysis shows that bicyclo[3.2.1]-DNA forms stable duplexes with complementary DNA, although generally with lower Tm values than pure DNA duplexes. Duplex formation is strictly constrained to antiparallel complementary sequences, and base-mismatch discrimination is slightly enhanced compared to pure DNA duplexes. In addition, bicyclo[3.2.1]-DNA sequences are resistant to a 3'-exonuclease. The furanose unit present in natural nucleosides is not necessary f...Continue Reading

Citations

Aug 20, 2010·Nucleic Acids Research·Damian IttigChristian J Leumann
Aug 18, 2006·Chemistry : a European Journal·Simon P Scheidegger, Christian J Leumann
Mar 3, 2021·Nature Communications·Karishma MatangeAlbert J Keung
Dec 13, 2001·Chemical Reviews·D J HillJ S Moore
Dec 11, 2003·Journal of the American Chemical Society·Jessica BecaudChristian J Leumann
Aug 18, 2009·Journal of the American Chemical Society·Ignacio FaustinoModesto Orozco

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