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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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7.1K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

4.5K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
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Protein Recognition by Functionalized Sulfonatocalix[4]arenes.

Aishling M Doolan1, Martin L Rennie1, Peter B Crowley1

  • 1School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 11, 2017
PubMed
Summary

Mono-functionalized sulfonatocalix[4]arenes show altered cytochrome c interactions. Substituents like bromo and phenyl groups influence binding modes and crystal packing, affecting protein recognition.

Keywords:
calixarenehalogen bondmolecular glueself-assemblystructural biology

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Area of Science:

  • Supramolecular Chemistry
  • Biophysical Chemistry
  • Structural Biology

Background:

  • Sulfonatocalix[4]arenes are macrocyclic compounds with versatile host-guest chemistry.
  • Cytochrome c is a crucial protein involved in cellular respiration and apoptosis.
  • Understanding host-protein interactions is vital for drug design and biomaterial development.

Purpose of the Study:

  • To investigate the impact of mono-functionalization on sulfonatocalix[4]arene interactions with cytochrome c.
  • To elucidate the structural and thermodynamic basis of these altered recognition events.
  • To explore novel binding modes and self-assembly mechanisms induced by functionalized calixarenes.

Main Methods:

  • X-ray crystallography was employed to determine high-resolution structures of calixarene-cytochrome c complexes.
  • Thermodynamic methods were utilized to quantify binding affinities and energetics.
  • Structural analysis focused on identifying specific interactions, including hydrogen bonds and halogen bonds.

Main Results:

  • Mono-functionalization with bromo or phenyl groups significantly altered cytochrome c recognition compared to the parent compound.
  • The bromo-substituted calixarene adopted a novel binding mode involving a self-encapsulated dimer and formed a weak halogen bond with cytochrome c.
  • The phenyl-substituted calixarene bound to Lys4 of cytochrome c, with crystal structures revealing ligand-ligand contacts suggesting assembly mechanisms.

Conclusions:

  • Functional group modification of sulfonatocalix[4]arenes provides a strategy to tune their recognition of proteins like cytochrome c.
  • The observed binding modes and self-assembly behaviors offer insights into supramolecular interactions at the protein interface.
  • These findings contribute to the rational design of tailored calixarene-based molecular recognition systems.