Nucleotides: Part LV - Synthesis and Application of a Novel Linker for Solid-Phase Synthesis of Modified Oligonucleotides

Article abstract of DOI:10.1002/hlca.19980810106

Various bifunctional amino-protecting groups such as the phthaloyl, succinyl, and glutaryl group were investigated as potential linker molecules for attachment to solid-support materials. Pentane-1,3,5-tricarboxylic acid 1,3-anhydride (16) offered the best properties and reacted with the amino groups of differently sugar-protected adenosine (see 20 and 22), cytidine (see 29), and guanosine derivatives (see 32) to the corresponding 2-(2-carhoxyethyl)glutaryl derivatives 23, 24, 30, and 33. The usefulness of the new linker-type molecules was demonstrated by the solid-support synthesis of the potentially antivirally active 3′-deoxyadenylyl-(2′-5′)-2′-adenylic acid 2′-{2-[(adenin-9-yl)methoxy]ethyl} ester (38) starting from the 2′-end with N⁶,N ⁶-[2-(2-carboxyethyl)glutaryl]-9-{{2-[(4,4′-dimethoxytrityl) oxy]ethoxy} methyl}adenine (12).