Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2009 Jun:Chapter 1:1.4.1-1.4.32.
doi: 10.1002/0471142700.nc0104s37.

Unnatural nucleosides with unusual base pairing properties

Donald E Bergstrom  1
Affiliations
Review

Unnatural nucleosides with unusual base pairing properties

Donald E Bergstrom. Curr Protoc Nucleic Acid Chem. 2009 Jun.

Abstract

Synthetic modified nucleosides designed to pair in unusual ways with natural nucleobases have many potential applications in biology and biotechnology. This overview lays the foundation for future protocol units on synthesis and application of unnatural bases, with particular emphasis on unnatural base analogs that mimic natural bases in size, shape, and biochemical processing. Topics covered include base pairs with alternative H-bonding schemes, dimensionally expanded base pairs, hydrophobic base pairs, metal-ligated bases, degenerate bases, universal nucleosides, and triplex constituents.

PubMed Disclaimer

References

Literature Cited

    1. Adelfinskaya, O., Wu, W., Davisson, V.J., and Bergstrom, D.E. 2005a. Synthesis and structural analysis of oxadiazole carboxamide deoxyribonucleoside analogs. Nucleosides Nucleotides Nucleic Acids 24:1919-1945.
    1. Adelfinskaya, O., Nashine, V.C., Bergstrom, D.E., and Davisson, V.J. 2005b. Efficient primer strand extension beyond oxadiazole carboxamide nucleobases. J. Am. Chem. Soc. 127:16000-16001.
    1. Aketani, S., Tanaka, K., Yamamoto, K., Ishihama, A., Cao, H., Tengeiji, A., Hiraoka, S., Shiro, M., and Shionoya, M. 2002. Syntheses and structure-activity relationships of nonnatural beta-C-nucleoside 5′-triphosphates bearing an aromatic nucleobase with phenolic hydroxy groups: Inhibitory activities against DNA polymerases. J. Med. Chem. 45:5594-5603.
    1. Atwell, S., Meggers, E., Spraggon, G., and Schultz, P.G. 2001. Structure of a copper-mediated base pair in DNA. J. Am. Chem. Soc. 123:12364-12367.
    1. Berdis, A.J. and McCutcheon, D. 2007. The use of non-natural nucleotides to probe template-independent DNA synthesis. Chembiochem 8:1399-1408.

LinkOut - more resources