Stability and selectivity of unnatural DNA with five-membered-ring nucleobase analogues.
In an effort to develop an orthogonal third base pair for the storage of genetic information, thiophene and furan heterocycles have been examined as nucleobase analogues. The stability of the unnatural bases was evaluated in duplex DNA paired opposite other unnatural bases as well as opposite the natural bases. Several unnatural base pairs are identified that are both reasonably stable and strongly selective against mispairing with native bases. These results expand the potential nucleobase analogues with which the genetic alphabet may be expanded to include five-membered-ring heterocycles.
Berger
Markus
M
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Luzzi
Scott D
SD
Henry
Allison A
AA
Romesberg
Floyd E
FE
D020137:Base Pair Mismatch; D020029:Base Pairing; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D013816:Thermodynamics; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry*
D005663:Furans; D006027:Glycosides; D009705:Nucleosides; D009841:Oligonucleotides; D013876:Thiophenes; D004247:DNA