Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

2'-O-[2-(guanidinium)ethyl]-modified oligonucleotides: stabilizing effect on duplex and triplex structures.

Thazha P Prakash1, Ask Püschl, Elena Lesnik

  • 1Department of Medicinal Chemistry, Isis Pharmaceuticals, Inc., Carlsbad, California 92008, USA.

Organic Letters
|June 5, 2004
PubMed
Summary

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

A Postsynthetic Strategy for Oligonucleotides Containing 2-Fluoro-adenine and Isoguanine Nucleobases.

Organic letters·2026
Same author

Synthesis and biophysical evaluation of C-5-triazolyl-functionalized morpholino-thymidine analogs.

Organic & biomolecular chemistry·2026
Same author

Acyclic serinol nucleic acid modification of siRNAs overcomes seed region mediated off-target effects while maintaining potency.

Nucleic acids research·2026
Same author

A metal ion-dependent mechanism promoting gain of function in NEIL1 variants.

International journal of radiation biology·2026
Same author

Synthesis of siRNAs containing carbocyclic nucleotides and the role of cyclopentane conformation in RNAi activity.

RSC chemical biology·2026
Same author

New targets and procedures for validating the valence geometry of nucleic acid structures.

Nucleic acids research·2026

Novel 2'-O-[2-(guanidinium)ethyl] (2'-O-GE) modified oligonucleotides show enhanced binding affinity and nuclease resistance. Their crystal structure reveals atomic details of this promising nucleic acid modification.

Area of Science:

  • Medicinal Chemistry
  • Molecular Biology
  • Biochemistry

Background:

  • Oligonucleotides are crucial in molecular biology and therapeutics.
  • Modifications can enhance oligonucleotide properties like stability and binding.
  • Developing novel oligonucleotide modifications is key for advancing nucleic acid-based technologies.

Purpose of the Study:

  • To synthesize oligonucleotides with a novel 2 acronym{'-O-[2-(guanidinium)ethyl] (2 acronym{'-O-GE) modification.
  • To evaluate the impact of the 2 acronym{'-O-GE modification on oligonucleotide binding affinity and nuclease stability.
  • To determine the crystal structure of a DNA duplex containing the 2 acronym{'-O-GE modification.

Main Methods:

  • Novel protecting group strategy for guanidinium group synthesis.

Related Experiment Videos

  • Thermal denaturation (Tm) assays to measure binding affinity.
  • Nuclease degradation assays.
  • X-ray crystallography to solve the duplex structure at 1.16 A resolution.

    • Main Results:

    • Successfully synthesized 2 acronym{'-O-GE modified oligonucleotides.
    • Demonstrated enhanced binding affinity to RNA and DNA duplexes (DeltaTm = 3.2 °C per modification).
    • Exhibited exceptional resistance to nuclease degradation.
    • Obtained high-resolution crystal structure of a modified DNA duplex.

    Conclusions:

    • The 2 acronym{'-O-GE modification significantly improves oligonucleotide binding affinity and stability.
    • These modified oligonucleotides show promise for therapeutic applications due to enhanced nuclease resistance.
    • The crystal structure provides valuable insights into the molecular basis of these improved properties.