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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
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Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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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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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Multicopper Clusters Enable Oxidative Phenol Macrocyclization (OxPM) of Peptides.

Anna Libman1, Mor Ben-Lulu1, Eden Gaster1

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Researchers developed a new biomimetic method using multicopper(II) clusters for synthesizing complex macrocyclic peptides, including vancomycin ring models. This efficient approach overcomes challenges in creating these vital antibiotic structures.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • Glycopeptide antibiotics like vancomycin are synthesized via enzymatic oxidative phenol macrocyclization.
  • Existing biomimetic methods for this transformation are not sufficiently simple or step-economical.

Purpose of the Study:

  • To develop a highly efficient and step-economical biomimetic method for synthesizing biaryl-bridged and diaryl ether-linked macrocyclic peptides.
  • To demonstrate the utility of multicopper(II) clusters in catalyzing challenging macrocyclization reactions.

Main Methods:

  • Utilized multicopper(II) clusters to promote intramolecular oxidative phenol coupling.
  • Developed selective synthesis conditions for macrocyclic peptides.
  • Synthesized ring models of vancomycin and the arylomycin cyclic core.

Main Results:

  • Achieved highly efficient synthesis of biaryl-bridged and diaryl ether-linked macrocyclic peptides.
  • Demonstrated the ability of multicopper(II) clusters to chelate diphenols and favor intramolecular coupling.
  • Successfully synthesized complex antibiotic macrocyclic peptide models.

Conclusions:

  • Multicopper(II) clusters offer a powerful catalytic system for biomimetic macrocyclization.
  • This technology facilitates the assembly of challenging complex antibiotic macrocyclic peptides.
  • Copper clusters can catalyze redox transformations beyond the scope of smaller metal catalysts.