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Unexpectedly stable artificial duplex from flexible acyclic threoninol

Asanuma, H.; Toda, T.; Murayama, K.; Liang, X.; Kashida, H.

Journal of the American Chemical Society 132(42): 14702-14703

2010


ISSN/ISBN: 1520-5126
PMID: 20886877
DOI: 10.1021/ja105539u
Accession: 056757369

A new foldamer, acyclic threoninol nucleic acid (aTNA), has been synthesized by tethering each of the genetic nucleobases A, G, C, and T to d-threoninol molecules, which were then incorporated as building blocks into a scaffold bearing phosphodiester linkages. We found that with its fully complementary strand in an antiparallel fashion, the aTNA oligomer forms an exceptionally stable duplex that is far more stable than corresponding DNA or RNA duplexes, even though single-stranded aTNA is rather flexible and thus does not take a preorganized structure.

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