2006•The Journal of Organic ChemistryRequires access

Base−Base Interactions in the Minor Groove of Double-Stranded DNA

Tongfei Wu, Koen Nauwelaerts, Arthur A. Van Aerschot, Matheus Froeyen, Eveline Lescrinier, Piet A. Herdewijn

Open publisher page 41 citations

Abstract

A method has been developed for the synthesis of bisheaded nucleosides with thymine and adenine base moieties. We have demonstrated that, when incorporated in oligonucleotides, extrahelical A-T base interactions are possible when the bisheaded nucleosides are positioned in opposite strands of the duplex and are separated from each other by one regular base pair.

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What this paper is about

A method has been developed for the synthesis of bisheaded nucleosides with thymine and adenine base moieties. We have demonstrated that, when incorporated in oligonucleotides, extrahelical A-T base interactions are possible when the bisheaded nucleosides are positioned in opposite strands of the duplex and are separated from each other by one regular base pair.

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Available abstract

A method has been developed for the synthesis of bisheaded nucleosides with thymine and adenine base moieties. We have demonstrated that, when incorporated in oligonucleotides, extrahelical A-T base interactions are possible when the bisheaded nucleosides are positioned in opposite strands of the duplex and are separated from each other by one regular base pair.

Key concepts: Minor groove, Base pair, Base (topology), Oligonucleotide, Duplex (building), Thymine, DNA, Groove (engineering)

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