Design of artificial nucleobases for the recognition of the AT inversion by triple-helix forming oligonucleotides: A structure-stability relationship study and neighbour bases effect

We report herein on the synthesis, the incorporation into triplex forming oligonucleotides (TFO) and the recognition properties of a series of synthetic nucleosides designed for the specific recognition of an inverted A x T base pair in a pyrimidine triple helix motif. These analogues were designed...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2003-07, Vol.11 (13), p.2751-2759
Main Authors: GUIANVARC'H, Dominique, FOURREY, Jean-Louis, MAURISSE, Rosalie, SUN, Jian-Sheng, BENHIDA, Rachid
Format: Article
Language:English
Subjects:
Adenine
Base Pairing
Base Sequence
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Nucleic Acid Conformation
Nucleosides, nucleotides and oligonucleotides
Oligodeoxyribonucleotides - chemical synthesis
Oligodeoxyribonucleotides - chemistry
Organic chemistry
Organophosphorus Compounds - chemical synthesis
Pliability
Preparations and properties
Thymine
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Summary:We report herein on the synthesis, the incorporation into triplex forming oligonucleotides (TFO) and the recognition properties of a series of synthetic nucleosides designed for the specific recognition of an inverted A x T base pair in a pyrimidine triple helix motif. These analogues were designed on the basis of the results obtained with our previously reported compounds S and B(t), in order to define a structure-stability relationship. We report also on the chemical nature effect of the bases flanking S in the case of S-containing TFOs, in order to get further informations about the recognition process within the A x TxS triplet. This study establishes guidelines for the conception of more potent analogues for the recognition of both A x T and G x C inverted base pairs.
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(03)00229-3