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Synlett 1999; 1999(S1): 940-944
DOI: 10.1055/s-1999-3112
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Pyranosyl-RNA Supramolecules Containing Non-Hydrogen Bonding Base-Pairs

Christian Hamon* , Tilmann Brandstetter, Norbert Windhab
  • *Department for Bio-Organic Systems, Aventis Research & Technologies, D-65926 Frankfurt am Main, Germany; Fax +49(69)30 58 15 35; E-mail: windhab@aventis.com
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Publication Date:
31 December 1999 (online)

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Synthesis and properties of a new pyranosyl-RNA nucleoside using tryptamine as nucleo-base is reported. Incorporation of this unit into oligomers using standard phosphoamidite chemistry yielded self-complementary and non-selfcomplementary oligonucleotide pairs. Thermal melting experiments of these examples showed the sequence dependent stabilising characteristics of the incorporated base in the symmetric pairing constitution with a standard Tm near that of a similar A-T-pair as well as pairing selectivity with respect to non-symmetric pairing tolerating thymine but destabilizing if confronted to an adenine as complementary base in the antiparallel strand.

N-glycosides - synthetic nucleotides - supramolecular chemistry - base pairing - nanotechnology

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