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Related Experiment Videos

Deoxypolypeptides bind and cleave RNA.

Liang Cheng1, Adaickapillai Mahendran1, Ruben L Gonzalez2

  • 1Department of Chemistry, Columbia University, New York, NY 10027.

Proceedings of the National Academy of Sciences of the United States of America
|May 21, 2014
PubMed
Summary
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L-deoxypolypeptides (DOPPs) show chiral binding to RNA and catalyze its cleavage, unlike their D-enantiomers. This suggests L-DOPPs offer a promising avenue for RNA-targeted therapeutics and biocatalysis.

Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Polymer Science

Background:

  • Chiral polyamines are novel biomaterials with potential applications.
  • Histidine-rich peptides are known to interact with nucleic acids.
  • Understanding stereospecific interactions is crucial for biomolecular design.

Purpose of the Study:

  • To synthesize and characterize L- and D-deoxypolypeptides (DOPPs) from polyhistidines.
  • To investigate the RNA binding and catalytic cleavage properties of these chiral DOPPs.
  • To elucidate the mechanism of RNA cleavage catalyzed by L-DOPP.

Main Methods:

  • Selective reduction of protected polyhistidines using borane.
  • Preparation of L- and D-deoxypolypeptides (DOPPs).
  • Assays for RNA binding and catalytic activity, including kinetic studies.
Keywords:
artificial enzymeschiral discriminationdeoxygenated peptidesnucleic acids binding

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Main Results:

  • L-octahistidine DOPP demonstrated cooperative binding to D-polyuridylic acid RNA, while D-octahistidine DOPP did not.
  • L-DOPP exhibited superior catalytic activity in cleaving RNA compared to D-DOPP.
  • Evidence suggests L-DOPP utilizes imidazole groups and backbone cations for bifunctional catalysis, possibly via a phosphorane intermediate.

Conclusions:

  • Stereochemistry significantly influences the RNA binding and catalytic properties of polyhistidine derivatives.
  • L-DOPP represents a promising chiral catalyst for RNA cleavage, with potential implications for ribonuclease mechanisms.
  • The proposed bifunctional catalytic mechanism involving imidazole groups and backbone cations offers new insights into RNA processing.