Studies toward Oxyacetamide-Linked RNA Analogues: Synthesis and Conformation of a Modified Dinucleoside

Dedicated to Prof. M. S. Wadia on the occasion of his 75^th birthday

Abstract

A new oxyacetamide-modified dinucleoside with 5′-(S) chirality, a hydrophobic 5′-C-(2-methoxyethyl) group, and a 2′-O-methyl group was synthesized from d-glucose. This dinucleoside showed a helical structure based on CD and NMR spectroscopy. The sugar puckering at the 5′ and 3′ ends were found to be ‘S’- and ‘N’-types, respectively. These results were substantiated by ab initio density functional theory.

Key words

modified dinucleoside - circular dichroism - oxyacetamide backbone - antisense agents - carbohydrates

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