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Related Concept Videos

Phosphodiester Linkages01:01

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Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
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The addition or removal of phosphate groups from proteins is the most common chemical modification that regulates cellular processes. These modifications can affect the structure, activity, stability, and localization of proteins within cells as well as their interactions with other proteins.
During phosphorylation, protein kinases transfer the terminal phosphate group of ATP to specific amino acid side chains of substrate proteins. Serine, threonine, and tyrosine are the most commonly...
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Synthetic Methods of Phosphonopeptides.

Jiaxi Xu1

  • 1State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.

Molecules (Basel, Switzerland)
|December 16, 2020
PubMed
Summary

Phosphonopeptides, phosphorus analogues of peptides, are key enzyme inhibitors and antigens. This review details synthetic methods for phosphonamidate bonds in phosphonopeptides, highlighting an efficient four-component condensation reaction.

Keywords:
peptidephosphonamidatephosphonopeptideβ-phosphonopeptideγ-phosphonopeptide

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Biochemistry

Background:

  • Phosphonopeptides are peptide analogs containing phosphorus.
  • They serve as crucial enzyme inhibitors and antigens for generating catalytic antibodies.
  • Common phosphonopeptides feature aminoalkylphosphonic acid residues, often with a phosphonamidate bond.

Purpose of the Study:

  • To review and focus on the synthetic methodologies for constructing phosphonamidate bonds within phosphonopeptides.
  • To highlight efficient and convergent strategies for phosphonopeptide synthesis.

Main Methods:

  • Traditional methods involve phosphonylation with phosphonochloridates, condensation reactions, and phosphinylation/oxidation.
  • A key alternative strategy discussed is the pseudo four-component condensation reaction.
  • This reaction efficiently synthesizes phosphonopeptides by forming aminoalkylphosphonic acids and the phosphonamidate bond simultaneously.

Main Results:

  • The review consolidates various synthetic routes for phosphonamidate bond formation in phosphonopeptides.
  • The pseudo four-component condensation reaction is presented as a convergent and efficient method.
  • This approach allows for the simultaneous construction of key structural features.

Conclusions:

  • The synthesis of phosphonopeptides, particularly those containing phosphonamidate bonds, has advanced through various chemical strategies.
  • The pseudo four-component condensation reaction offers a powerful and efficient route for accessing these important molecules.
  • Understanding these synthetic methods is crucial for their application in medicinal chemistry and antibody generation.