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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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Proteins can undergo many types of post-translational modifications, often in response to changes in their environment. These modifications play an important role in the function and stability of these proteins. Covalently linked molecules include functional groups, such as methyl, acetyl, and phosphate groups, and also small proteins, such as ubiquitin. There are around 200 different types of covalent regulators that have been identified.
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In the plasma membrane, the lipids forming the bilayer can also act as an anchor to tether proteins to the membrane. The three main types of lipid anchors found in eukaryotes are – prenyl groups, fatty acyl groups, and glycosylphosphatidylinositol or GPI groups. Prenyl and fatty acyl groups act as anchors on the cytosolic surface of the membrane, whereas GPI anchors proteins on the extracellular side.
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Hydrocarbon stapled peptides as modulators of biological function.

Philipp M Cromm1,2, Jochen Spiegel1,2, Tom N Grossmann1,2,3

  • 1†Max Planck Institute of Molecular Physiology, Otto-Hahn-Str. 11, 44227 Dortmund, Germany.

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Modified peptides, like hydrocarbon stapled α-helical peptides, are emerging as a promising therapeutic class. These stabilized peptides can target previously undruggable disease-related protein-protein interactions (PPIs).

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Area of Science:

  • Medicinal Chemistry
  • Drug Discovery
  • Biochemistry

Background:

  • Peptide therapeutics face challenges like poor stability and bioavailability.
  • Chemical modifications and unnatural amino acids enhance peptide drug properties.
  • Modified peptides bridge the gap between small molecules and biologics.

Purpose of the Study:

  • To provide a comprehensive overview of hydrocarbon stapled α-helical peptides.
  • To discuss the development and applications of this novel therapeutic class.
  • To analyze the benefits and limitations of hydrocarbon stapling.

Main Methods:

  • Review of existing literature on peptide modifications and stabilization techniques.
  • Focus on hydrocarbon stapling for α-helical peptide stabilization.
  • Analysis of structure-activity relationships and therapeutic potential.

Main Results:

  • Hydrocarbon stapled peptides offer enhanced stability and cell permeability.
  • They are effective in inhibiting disease-relevant protein-protein interactions (PPIs).
  • This approach enables targeting previously 'undruggable' targets.

Conclusions:

  • Hydrocarbon stapled peptides represent a significant advancement in peptide drug discovery.
  • This technique overcomes limitations of traditional peptides, offering a promising therapeutic avenue.
  • Further research into their development and application is warranted.