Synthesis of A Branched Locked Nucleic Acid (LNA) Analogue

Abstract

A 3′-C-branched LNA-type bicyclic nucleoside, containing a furanose ring locked in an N-type conformation, was synthesized from a known 3-C-vinyl allofuranose derivative using a strategy relying on the condensation with the nucleobase after the introduction of the branching hydroxymethyl chain by our recently developed RuO₄ based protocol. This branched LNA nucleoside has a potential as a monomer for the functionalization of LNA.

Keywords:

• Locked nucleic acid
• N-type conformation
• RuO₄ oxidation

The work was supported by the Sixth Framework Program Marie Curie Host Fellowships for Early Stage Research Training under contract MEST-CT-2004-504018, by the Danish Natural Research Council and by the Nucleic Acid Center, which is funded by the Danish Natural Research Foundation for studies on nucleic acid chemical biology.