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

Authors
Robins, MJ Doboszewski, B Nilsson, BL Peterson, MA
Citation
Mj. Robins et al., Synthesis of amide-linked [(3 ')CH2CO-NH(5 ')] nucleoside analogues of small oligonucleotides, NUCLEOS NUC, 19(1-2), 2000, pp. 69-86
Citations number
29
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
ISSN journal
15257770 → ACNP
Volume
19
Issue
1-2
Year of publication
2000
Pages
69 - 86
Database
ISI
SICI code
1525-7770(2000)19:1-2<69:SOA[''>2.0.ZU;2-F
Abstract
We report syntheses of new amide-linked (di-penta)nucleoside analogues of a ntisense oligonucleotide components. Solution-phase coupling of 3'-(carboxy methyl)-3'-deoxy- and 5'-amino-5'-deoxynucleoside derivatives provides amid e dimers. Activated [3'-(carboxymethyl)-3'-deoxy] units with a 5'-azido-5'- deoxy function provide "masked" 5'-amino-5'-deoxy residues for chain extens ion, and a 5'-O-DMT-protected unit provides the 5'-terminus far attachment to a phosphodiester linkage.