Synthesis of amide-linked [(3')CH2CO-NH(5')] nucleoside analogues of small oligonucleotides

M J Robins; B Doboszewski; B L Nilsson; M A Peterson

doi:10.1080/15257770008032997

Synthesis of amide-linked [(3')CH2CO-NH(5')] nucleoside analogues of small oligonucleotides

Nucleosides Nucleotides Nucleic Acids. 2000 Jan-Feb;19(1-2):69-86. doi: 10.1080/15257770008032997.

Authors

M J Robins¹, B Doboszewski, B L Nilsson, M A Peterson

Affiliation

¹ Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.

PMID: 10772703
DOI: 10.1080/15257770008032997

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Nucleosides / chemical synthesis*
Nucleosides / chemistry
Oligonucleotides / chemistry*
Oligonucleotides, Antisense / chemistry*

Substances

Amides
Nucleosides
Oligonucleotides
Oligonucleotides, Antisense