Synthesis of 2′- O-[2-[( N, N-dialkylamino)oxy]ethyl]-modified oligonucleotides: hybridization affinity, resistance to nuclease, and protein binding characteristics

Synthesis of a series of 2′- O-[2-[( N, N-dialkylamino)oxy]ethyl]-modified 5-methyluridine nucleoside phosphoramidites and solid supports are described. Using these monomers, modified oligonucleotides containing phosphodiester linkages were synthesized in high yields. These modified oligonucleotides...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2003-09, Vol.59 (37), p.7413-7422
Main Authors: Prakash, Thazha P, Kawasaki, Andrew M, Lesnik, Elena A, Sioufi, Namir, Manoharan, Muthiah
Format: Article
Language:English
Subjects:
hybridization affinity
nuclease resistance
protein binding
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Synthesis of a series of 2′- O-[2-[( N, N-dialkylamino)oxy]ethyl]-modified 5-methyluridine nucleoside phosphoramidites and solid supports are described. Using these monomers, modified oligonucleotides containing phosphodiester linkages were synthesized in high yields. These modified oligonucleotides showed enhanced binding affinity to the complementary RNA (and not to DNA) and excellent nuclease stability with t 1/2>24 h. The human serum albumin binding properties of modified oligonucleotides have been evaluated to assess their transport and toxicity properties. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)01104-9