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Meso-oligodeoxyribonucleotides

O N Iwanami1, K Shudo, Y Hashimoto

  • 1Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.

Nucleic Acids Symposium Series
|January 1, 1993
PubMed
Summary
This summary is machine-generated.

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Meso-DNAs, modified oligonucleotides with alternating L- and D-sugars, exhibit phosphodiesterase resistance. These novel nucleic acids show distinct binding preferences, with LD-(dA)n forming triplexes and being RNA-selective, while LD-(dT)n forms duplexes and is DNA-selective.

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Synthetic Chemistry

Background:

  • Natural DNA and enantiomeric DNA (L-DNA) are crucial for genetic information storage and transfer.
  • Modified oligonucleotides are being explored for therapeutic applications and to understand DNA structure-function relationships.
  • Phosphodiesterase resistance is a desirable trait for oligonucleotide stability in biological systems.

Purpose of the Study:

  • To synthesize and characterize meso-DNAs, a novel class of modified oligonucleotides with alternating L- and D-sugar backbones.
  • To investigate the biochemical properties, including nuclease resistance and binding interactions, of meso-DNAs.
  • To explore the DNA/RNA selectivity and complex formation modes of specific meso-DNA sequences, LD-(dA)n and LD-(dT)n.

Main Methods:

Related Experiment Videos

  • Synthesis of meso-oligonucleotides (LD-(dN)n) with alternating L- and D-sugar residues.
  • Analysis of meso-DNA characteristics, focusing on LD-(dA)n and LD-(dT)n.
  • Assessment of phosphodiesterase resistance.
  • Investigation of binding interactions with complementary homopolymers (natural DNA and RNA).
  • Circular Dichroism (CD) spectroscopy to analyze conformational properties.

Main Results:

  • Meso-DNAs, specifically LD-(dA)n and LD-(dT)n, were successfully prepared.
  • These L-sugar containing oligomers demonstrated resistance to phosphodiesterases.
  • LD-(dA)n preferentially formed triplexes with its complementary homopolymer, whereas LD-(dT)n formed only duplexes.
  • LD-(dA)n exhibited RNA selectivity (stronger binding to poly U than poly dT), while LD-(dT)n showed DNA selectivity (stronger binding to poly dA than poly A).
  • CD spectra indicated that meso-DNA/natural polymer complexes adopt conformations similar to natural right-handed helices.

Conclusions:

  • Meso-DNAs represent a novel class of modified oligonucleotides with unique structural and binding properties.
  • The alternating L- and D-sugar backbone confers phosphodiesterase resistance.
  • Differential complex formation (triplex vs. duplex) and nucleic acid selectivity (RNA vs. DNA) were observed between LD-(dA)n and LD-(dT)n, highlighting sequence-dependent behavior.
  • Meso-DNAs maintain a conformationally stable structure resembling natural DNA helices.