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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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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Pericyclic Reactions: Introduction01:17

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
3.5K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.0K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Sequence-defined bioactive macrocycles via an acid-catalysed cascade reaction.

Mintu Porel1, Dana N Thornlow1, Ngoc N Phan1

  • 1School of Chemical and Biomolecular Engineering, Cornell University, 120 Olin Hall, Ithaca, New York 14850, USA.

Nature Chemistry
|May 25, 2016
PubMed
Summary

Synthetic macrocycles called oligothioetheramides (oligoTEAs) were synthesized using a novel cascade reaction. These novel macrocycles show potent antibacterial activity, offering a new therapeutic avenue for drug discovery.

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Area of Science:

  • Synthetic chemistry
  • Medicinal chemistry
  • Macromolecular science

Background:

  • Sequence-defined oligomers offer tunable synthetic macrocycles.
  • Incorporating bioactive side chains into macromolecules enhances pharmacological relevance.
  • Peptides and peptidomimetics are important drug scaffolds.

Purpose of the Study:

  • To report the synthesis of novel oligothioetheramide (oligoTEA) macrocycles.
  • To demonstrate the versatility and modularity of the oligoTEA synthesis.
  • To evaluate the biological activity of oligoTEA macrocycles as antimicrobial agents.

Main Methods:

  • One-pot acid-catalyzed cascade reaction for macrocyclization.
  • Synthesis of over 20 diverse oligoTEA macrocycles.
  • Structural characterization using NMR spectroscopy.
  • Design and testing of oligoTEAs mimicking antimicrobial peptides.

Main Results:

  • Successful synthesis of diverse oligothioetheramide macrocycles.
  • NMR analysis revealed conformational isomers and local chain dynamics.
  • Designed oligoTEAs demonstrated potent antibacterial activity against Gram-positive and Gram-negative bacteria.
  • Activity observed with minimal cationic charge centers (2-3).

Conclusions:

  • Oligothioetheramide macrocycles represent a versatile class of synthetic macromolecules.
  • The developed cascade reaction enables efficient and modular synthesis.
  • Macrocyclic oligoTEAs show promise as novel antimicrobial agents.