{"controller"=>"catalog", "action"=>"show", "locale"=>"en", "id"=>"255938499"}
  • EN
  • DA

Danish NationalResearch Database

  • Search Publications & Researchers
  • Open Access Indicator
  • Publications
  • Researchers
Example Finds records
water{} containing the word "water".
water supplies"{}" containing the phrase "water supplies".
author:"Doe, John"author:"{}" containing the prase "Doe, John" in the author field.
title:IEEEtitle:{} containing the word "IEEE" in the title field.
Need more help? Advanced search tutorial
  • Selected (0)
  • History

Synthesis and Characterization of Oligodeoxyribonucleotides Modified with 2'-Amino-α-l-LNA Adenine Monomers

    • Save to Mendeley
    • Export to BibTeX
    • Export to RIS
    • Email citation
Authors:
  • Andersen, Nicolai K ;
    Close
    Department of Physics, Chemistry and Pharmacy, Faculty of Science, SDU
  • Anderson, Brooke A ;
    Close
    unknown
  • Wengel, Jesper ;
    Close
    Orcid logo0000-0001-9835-1009
    Department of Physics, Chemistry and Pharmacy, Faculty of Science, SDU
  • Hrdlicka, Patrick J
    Close
    unknown
Subtitle:
High-Affinity Targeting of Single-Stranded DNA
DOI:
10.1021/jo4022937
Abstract:
The development of conformationally restricted nucleotide building blocks continues to attract considerable interest because of their successful use within antisense, antigene, and other gene-targeting strategies. Locked nucleic acid (LNA) and its diastereomer α-l-LNA are two interesting examples thereof. Oligonucleotides modified with these units display greatly increased affinity toward nucleic acid targets, improved binding specificity, and enhanced enzymatic stability relative to unmodified strands. Here we present the synthesis and biophysical characterization of oligodeoxyribonucleotides (ONs) modified with 2'-amino-α-l-LNA adenine monomers W-Z. The synthesis of the target phosphoramidites 1-4 is initiated from pentafuranose 5, which upon Vorbrüggen glycosylation, O2'-deacylation, O2'-activation and C2'-azide introduction yields nucleoside 8. A one-pot tandem Staudinger/intramolecular nucleophilic substitution converts 8 into 2'-amino-α-l-LNA adenine intermediate 9, which after a series of nontrivial protecting-group manipulations affords key intermediate 15. Subsequent chemoselective N2'-functionalization and O3'-phosphitylation give targets 1-4 in ∼1-3% overall yield over 11 steps from 5. ONs modified with pyrene-functionalized 2'-amino-α-l-LNA adenine monomers X-Z display greatly increased affinity toward DNA targets (ΔTm/modification up to +14 °C). Results from absorption and fluorescence spectroscopy suggest that the duplex stabilization is a result of pyrene intercalation. These characteristics render N2'-pyrene-functionalized 2'-amino-α-l-LNAs of considerable interest for DNA-targeting applications.
Type:
Journal article
Language:
English
Published in:
Journal of Organic Chemistry, 2013, Vol 78, Issue 24, p. 12690-12702
Main Research Area:
Science/technology
Publication Status:
Published
Review type:
Peer Review
Submission year:
2013
Scientific Level:
Scientific
ID:
255938499

Full text access

  • Doi Get publisher edition via DOI resolver
Checking for on-site access...

On-site access

At institution

  • University southern denmark

Metrics

Feedback

Sitemap

  • Search
    • Statistics
    • Tutorial
    • Data
    • FAQ
    • Contact
  • Open Access
    • Overview
    • Development
    • FAQ
    • Contact
  • About
    • Institutions
    • Release History
    • Cookies and privacy policy

Copyright © 1998–2018.

Fivu en