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Related Experiment Videos

Oligonucleotide N3'-->P5' phosphoramidates

S M Gryaznov1, D H Lloyd, J K Chen

  • 1Lynx Therapeutics, Inc., Hayward, CA 94545, USA.

Proceedings of the National Academy of Sciences of the United States of America
|June 20, 1995
PubMed
Summary

Modified oligodeoxyribonucleotide phosphoramidates form highly stable DNA and RNA duplexes and triplexes. These synthetic oligonucleotides offer enhanced thermal stability, showing promise for therapeutic and diagnostic applications.

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Area of Science:

  • Chemical Biology
  • Nucleic Acid Chemistry
  • Biochemistry

Background:

  • Synthetic oligonucleotides are crucial for developing targeted therapeutics and diagnostics.
  • Oligonucleotide analogs with modified internucleoside linkages are of significant interest.
  • N3'-->P5' phosphoramidates represent a novel class of modified oligonucleotides.

Purpose of the Study:

  • To synthesize uniformly modified oligodeoxyribonucleotide N3'-->P5' phosphoramidates.
  • To investigate the hybridization properties and structural characteristics of these modified oligonucleotides.
  • To evaluate their potential as therapeutic and diagnostic agents.

Main Methods:

  • Synthesis of N3'-->P5' phosphoramidate-modified oligodeoxyribonucleotides.
  • Thermal dissociation (Tm) experiments to assess duplex stability.

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  • Circular Dichroism (CD) spectroscopy to determine structural conformation.
  • Triplex formation assays under physiological conditions.

    • Main Results:

    • Phosphoramidate-modified oligonucleotides formed highly stable duplexes with DNA, RNA, and self.
    • Duplex thermal stability increased by 2.2-2.6 °C per modified linkage compared to phosphodiesters.
    • CD spectroscopy indicated an A-form structure similar to RNA.
    • Stable triplexes were formed with double-stranded DNA under physiological conditions, outperforming natural phosphodiesters.

    Conclusions:

    • N3'-->P5' phosphoramidates exhibit enhanced hybridization properties and stability compared to natural oligonucleotides.
    • These modified oligonucleotides adopt an A-form structure, similar to RNA.
    • Their ability to form stable triplexes under physiological conditions highlights their potential in therapeutic applications.