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Synthesis of amide-linked [(3')CH2CO-NH(5')] nucleoside analogues of small oligonucleotides
M J Robins1, B Doboszewski, B L Nilsson
1Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Nucleosides, Nucleotides & Nucleic Acids
|April 25, 2000
Abstract:
We report syntheses of new amide-linked (di-penta)nucleoside analogues of antisense oligonucleotide components. Solution-phase coupling of 3'-(carboxymethyl)-3'-deoxy- and 5'-amino-5'-deoxynucleoside derivatives provides amide dimers. Activated [3'-(carboxymethyl)-3'-deoxy] units with a 5'-azido-5'-deoxy function provide "masked" 5'-amino-5'-deoxy residues for chain extension, and a 5'-O-DMT-protected unit provides the 5'-terminus for attachment to a phosphodiester linkage.