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Asseline, U ; Chassignol, M ; Draus, J ; Durand, M ; Maurizot, JC

Synthesis and properties of oligo-2 ’-deoxyribonucleotides containing internucleotidic phosphoramidate linkages modified with pendant groups ending with either two amino or two hydroxyl functions

Bioorganic & Medicinal Chemistry 11 (16) 3499-3511

par Administrateur - publié le

Abstract :

Single and multiple incorporations of stereochemically pure modified dinucleoside-phosphoramidates involving substituent groups ending with bis-hydroxyethyl and bis-aminoethyl groups have been performed into pyrimidic triple helix-forming oligo-2’-deoxyribonucleotides designed to bind parallel to the purine strand of the DNA target. The ability of these modified oligo-2’-deoxyribonucleotides to form triple helices has been studied by UV-melting curve analyses, and circular dichroism. Only the oligonucleotides involving modified phosphate groups with the Rp configuration formed more stable triple helices than did the parent phosphodiester sequences.