Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 6, Pages 1495-1499Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303867
Keywords
base pairing; circular dichroism; DNA; heterocycles; Janus bases
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Funding
- NSERC
- Banting Postdoctoral Fellowship program
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Janus bases are heterocyclic nucleic acid base analogs that present two different faces able to simultaneously hydrogen bond to nucleosides that form Watson-Crick base pairs. The synthesis of a Janus-AT nucleotide analogue, (N)J(AT), that has an additional endocyclic ring nitrogen and is thus more capable of efficiently discriminating T/A over G/C bases when base-pairing in a standard duplex-DNA context is described. Conversion to a phosphoramidite ultimately afforded incorporation into an oligonucleotide. In contrast to the first generation of carbocyclic Janus heterocycles, it remains in its unprotonated state at physiological pH and, therefore, forms very stable Watson-Crick base pairs with either A or T bases. Biophysical and computational methods indicate that (N)J(AT) is an improved candidate for sequence-specific genome targeting.
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