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Related Concept Videos

Peptide Bonds02:43

Peptide Bonds

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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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Protein Folding01:25

Protein Folding

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Proteins are chains of amino acids linked together by peptide bonds. Upon synthesis, a protein folds into a three-dimensional conformation, critical to its biological function. Interactions between its constituent amino acids guide protein folding, and hence the protein structure is primarily dependent on its amino acid sequence.
Protein Structure Is Critical to Its Biological Function
Proteins perform a wide range of biological functions such as catalyzing chemical reactions, providing...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Protein Organization01:24

Protein Organization

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Proteins are polymers of amino acid residues. They are versatile and responsible for different cellular functions, including DNA replication, molecular transport, catalysis, and structural support. Proteins have a hierarchical structure comprising at least three levels of organization: primary, secondary, and tertiary structure. Some large proteins have a quaternary structure where individual protein subunits are linked together.
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Updated: Oct 9, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Peptide cyclisation promoted by supramolecular complex formation.

Arnout P T Hartendorp1, Felix J de Zwart1, Hans Bieräugel1

  • 1Van't Hoff Institute for Molecular Sciences (HIMS), Science Park 904, 1098 XH Amsterdam, The Netherlands. j.h.vanmaarseveen@uva.nl.

Organic & Biomolecular Chemistry
|December 22, 2021
PubMed
Summary
This summary is machine-generated.

Sterically shielding metallo-porphyrins, like ZnTPP, facilitate the cyclisation of difficult dipeptides. This method enhances cyclic dipeptide yields by preventing unwanted intermolecular reactions during synthesis.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Synthetic Chemistry

Background:

  • Cyclic dipeptides are valuable scaffolds in medicinal chemistry.
  • The synthesis of cyclic dipeptides can be challenging due to competing intermolecular reactions.
  • Phenol ester activation is a common strategy, but often leads to low yields for sterically hindered substrates.

Purpose of the Study:

  • To develop a novel method for efficient cyclisation of reluctant dipeptides.
  • To investigate the use of sterically shielding metallo-porphyrins in peptide synthesis.
  • To improve the yield of cyclic dipeptides through controlled intermolecular reactions.

Main Methods:

  • Utilisation of sterically shielding metallo-porphyrins, specifically Zinc Tetraphenylporphyrin (ZnTPP).
  • Employing Staudinger-mediated cyclisation reactions.
  • Characterisation of ZnTPP binding to dipyridine-functionalised phenolic esters using Nuclear Magnetic Resonance (NMR) titrations and molecular modelling.

Main Results:

  • Successful cyclisation of phenol ester activated dipeptides was achieved using ZnTPP.
  • NMR titrations and modelling confirmed the binding interaction between ZnTPP and the activating ester.
  • The yield of the cyclic dipeptide increased significantly from 16% to 40% in the presence of ZnTPP.

Conclusions:

  • Sterically shielding metallo-porphyrins are effective tools for promoting intramolecular cyclisation in peptide synthesis.
  • ZnTPP can suppress unwanted intermolecular reactions, leading to higher yields of cyclic dipeptides.
  • This methodology offers a promising route for the synthesis of complex cyclic peptide structures.