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Related Concept Videos

Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

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Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
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A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
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In vitro Methylation Assay to Study Protein Arginine Methylation
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in,in-Cyclophanes with Bridgehead Methyl Groups.

Yonglong Xiao1, Joel T Mague1, Robert A Pascal1

  • 1Department of Chemistry , Tulane University , New Orleans , Louisiana 70118 , United States.

Organic Letters
|April 21, 2018
PubMed
Summary

Two novel cyclophane molecules with methyl groups in their cavities were synthesized and structurally analyzed. This research reveals unique molecular interactions and introduces the first macrobicyclic compound with two inward-facing methyl groups.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Cyclophanes are cyclic organic molecules known for their unique structural properties.
  • Understanding the spatial arrangement of substituents within cyclophane cavities is crucial for predicting their chemical behavior and applications.

Purpose of the Study:

  • To synthesize novel in,in-cyclophanes featuring methyl groups within their central cavities.
  • To elucidate the three-dimensional structures of these cyclophanes using X-ray crystallography.
  • To investigate the nature of nonbonded interactions and the structural novelty of these compounds.

Main Methods:

  • Synthesis of two distinct in,in-cyclophane derivatives.
  • Single-crystal X-ray diffraction analysis to determine molecular structures.
  • Analysis of nonbonded contacts and conformational features.

Main Results:

  • Successful synthesis and structural determination of two in,in-cyclophanes.
  • Identification of a very short nonbonded hydrogen-methyl group contact in one cyclophane.
  • Characterization of the first macrobicyclic compound featuring two inwardly directed methyl groups.

Conclusions:

  • The synthesized cyclophanes exhibit unique structural characteristics due to the presence of internal methyl groups.
  • Short nonbonded contacts can occur within cyclophane cavities, influencing molecular packing and properties.
  • The discovery of the novel macrobicyclic compound expands the scope of known cyclophane architectures.