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Related Concept Videos

Conjugated Proteins02:50

Conjugated Proteins

Simple proteins and protein complexes contain only amino acids. In contrast, many other proteins, called conjugated proteins, covalently bond with non-protein moieties.
Nucleoproteins are protein complexes that contain nucleic acids, categorized as deoxyribonucleoproteins (DNPs) or ribonucleoproteins (RNPs) respectively. The nucleosome is a typical example of a DNP where nuclear DNA is associated with histone proteins. The major antigen for the Covid-19 virus SARS-CoV is an RNP that is critical...
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Peptide Bonds

A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Ligand Binding and Linkage

Allosteric proteins have more than one ligand binding site; the binding of a ligand to any of these sites influences the binding of ligands to the other sites. When a protein is allosteric, its binding sites are called coupled or linked.  In the case of enzymes, the site that binds to the substrate is known as the active site and the other site is known as the regulatory site. When a ligand binds to the regulatory site, this leads to conformational changes in the protein that can influence the...

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Peptide-LNA oligonucleotide conjugates.

I Kira Astakhova1, Lykke Haastrup Hansen, Birte Vester

  • 1Nucleic Acid Center and the Biomolecular Nanoscale Engineering Center, Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark. ias@sdu.dk

Organic & Biomolecular Chemistry
|May 18, 2013
PubMed
Summary
This summary is machine-generated.

Internally attaching peptides to oligonucleotides via click chemistry enhances their binding affinity, selectivity, and stability for nucleic acid delivery and therapy. This novel approach improves biomolecular recognition by synthetic nucleic acid analogues.

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Area of Science:

  • Bioconjugation Chemistry
  • Medicinal Chemistry
  • Oligonucleotide Therapeutics

Background:

  • Peptide-oligonucleotide conjugates (POCs) are recognized for nucleic acid delivery and therapy.
  • Internal peptide attachment to oligonucleotides is less explored but offers potential for improved properties.

Purpose of the Study:

  • To develop a convenient method for preparing internally labeled POCs.
  • To enhance the biomedical properties of POCs through internal peptide conjugation.

Main Methods:

  • Utilized a 2 eal-alkyne-2 eal-amino-LNA scaffold for peptide introduction into oligonucleotides.
  • Employed copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) "click" chemistry for conjugation.
  • Incorporated model peptides (methionine- and leucine-enkephalins) into LNA/DNA strands.

Main Results:

  • Internal peptide attachment significantly improved DNA/RNA target binding affinity and selectivity compared to controls.
  • Circular dichroism (CD) measurements confirmed no structural distortion of the duplex by incorporated peptides.
  • Human serum studies demonstrated superior stability of the POCs over LNA/DNA mixmers and unmodified DNA.

Conclusions:

  • Internal peptide conjugation is a viable strategy to enhance the performance of synthetic nucleic acid analogues.
  • The developed method provides a convenient route for preparing internally labeled POCs with improved biomedical characteristics.
  • Molecular modeling indicated favorable interactions stabilizing the peptide-oligonucleotide structure.