PMID: 8972851Dec 1, 1996Paper

Watson-Crick base-pairing properties of bicyclo-DNA

Nucleic Acids Research
M BolliChristian J Leumann

Abstract

A series of sequences of the DNA analog bicyclo-DNA, 6-12 nucleotides in length and containing all four natural nucleobases, were prepared and their Watson-Crick pairing properties with complementary RNA and DNA, as well as in its own series, were analyzed by UV-melting curves and CD-spectroscopy. The results can be summarized as follows: bicyclo-DNA forms stable Watson-Crick duplexes with complementary RNA and DNA, the duplexes with RNA generally being more stable than those with DNA. Pyrimidine-rich bicyclo-DNA sequences form duplexes of equal or slightly increased stability with DNA or RNA, whereas purine-rich sequences show decreased affinity to complementary DNA and RNA when compared with wild-type (DNA-DNA, DNA-RNA) duplexes. In its own system, bicyclo-DNA prefers antiparallel strand alignment and strongly discriminates for base mismatches. Duplexes are always inferior in stability compared with the natural ones. A detailed analysis of the thermodynamic properties was performed with the sequence 5'-GGATGGGAG-3'x 5'-CTCCCATCC-3' in both backbone systems. Comparison of the pairing enthalpy and entropy terms shows an enthalpic advantage for DNA association (delta deltaH = -18 kcal x (mol)-1)) and an entropic advantage for bi...Continue Reading

References

Apr 1, 1981·Proceedings of the National Academy of Sciences of the United States of America·H R DrewR E Dickerson
Jul 9, 1993·Journal of Medicinal Chemistry·J F MilliganJ C Martin
Mar 1, 1996·Chemistry & Biology·M BolliC J Leumann

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Citations

Dec 7, 2007·Nucleosides, Nucleotides & Nucleic Acids·Tomohisa OsakiTakeshi Imanishi
May 29, 2003·Nucleic Acids Research·Su Jeong Kim, Byeang Hyean Kim
May 16, 2014·The Journal of Organic Chemistry·Pawan KumarPatrick J Hrdlicka
May 7, 2014·The Journal of Organic Chemistry·Pawan KumarPatrick J Hrdlicka
Jan 16, 2014·The Journal of Organic Chemistry·Branislav Dugovic, Christian J Leumann
Aug 10, 2004·Chembiochem : a European Journal of Chemical Biology·Dorte Renneberg, Christian J Leumann
Aug 30, 2008·Chembiochem : a European Journal of Chemical Biology·Samuel Luisier, Christian J Leumann
Apr 25, 2013·Chemistry : a European Journal·Anna-Barbara Gerber, Christian J Leumann
Apr 1, 2011·Chembiochem : a European Journal of Chemical Biology·Montserrat TerrazasRamon Eritja
Mar 7, 2017·Chemistry : a European Journal·Damien Evéquoz, Christian J Leumann
Sep 7, 2018·Organic & Biomolecular Chemistry·Chandan PalTushar Kanti Chakraborty
Aug 4, 2006·Organic & Biomolecular Chemistry·Andreas SchmidtFrancisco Javier Ramirez
Jan 16, 2019·Beilstein Journal of Organic Chemistry·Sibylle FreiChristian J Leumann
Mar 20, 2010·Chemical Reviews·Jacques LebretonChristophe Len
Jun 8, 2007·Journal of the American Chemical Society·Puneet SrivastavaJyoti Chattopadhyaya

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