Evaluation of oligonucleotides containing two novel 2'-O-methyl modified nucleotide monomers: a 3'-C-allyl and a 2'-O,3'-C-linked bicyclic derivative

H M Pfundheller; A A Koshkin; C E Olsen; J Wengel

doi:10.1080/07328319908044861

Evaluation of oligonucleotides containing two novel 2'-O-methyl modified nucleotide monomers: a 3'-C-allyl and a 2'-O,3'-C-linked bicyclic derivative

Nucleosides Nucleotides. 1999 Sep;18(9):2017-30. doi: 10.1080/07328319908044861.

Authors

H M Pfundheller¹, A A Koshkin, C E Olsen, J Wengel

Affiliation

¹ Department of Chemistry, University of Southern Denmark, Odense University, Denmark.

PMID: 10549150
DOI: 10.1080/07328319908044861

Abstract

The two ribo-configured nucleosides 1-(3-C-allyl-2-O-methyl-beta-D-ribo-pentofuranosyl)thymine 3 and (1S,5R,6R,8R)-5-hydroxy-6-(hydroxymethyl)-1-methoxy-8-(thymin-1-yl )- 2,7-dioxabicyclo[3.3.0]octane 6 have been transformed into their corresponding phosphoramidites, 5 and 8 respectively, and used as building blocks for the synthesis of modified oligonucleotides. The oligonucleotides were shown to hybridize with decreased binding affinity towards complementary single stranded DNA and RNA.

Publication types

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

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
DNA, Single-Stranded / chemistry
Molecular Structure
Nucleic Acid Denaturation
Nucleic Acid Heteroduplexes / chemistry
Nucleic Acid Hybridization
Oligoribonucleotides / chemical synthesis*
RNA / chemistry
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

Bridged Bicyclo Compounds, Heterocyclic
DNA, Single-Stranded
Nucleic Acid Heteroduplexes
Oligoribonucleotides
RNA