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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.8K
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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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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Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

4.7K
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,...
4.7K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.2K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.2K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

5.7K
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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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Sulfur Switches for Responsive Peptide Materials.

Timothy J Deming1,2

  • 1Department of Bioengineering, University of California, Los Angeles, California 90095, United States.

Accounts of Chemical Research
|February 19, 2024
PubMed
Summary
This summary is machine-generated.

Synthetic peptide materials with switchable properties are being developed using sulfur chemistry. These novel materials offer potential for advanced biomedical applications by responding to biological stimuli.

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Area of Science:

  • Biomaterials Science
  • Synthetic Chemistry
  • Biochemistry

Background:

  • Peptide-based materials mimic natural biological assemblies for applications like cell grafting and drug delivery.
  • Stimuli-responsive materials are crucial for dynamic biological interactions.
  • Sulfur chemistry in amino acids regulates biological processes and inspires synthetic material design.

Purpose of the Study:

  • To explore the development of peptide materials with switchable properties using sulfur chemistry.
  • To review sulfur switch mechanisms in biological systems and synthetic peptide materials.
  • To highlight recent advancements and applications of reversible sulfur switches in peptide materials.

Main Methods:

  • Incorporation of sulfur atoms (e.g., cysteine, methionine) into peptide structures.
  • Utilizing redox and alkylation reactions of sulfur-containing residues.
  • Designing synthetic peptide materials with noncanonical sulfur-containing amino acids.

Main Results:

  • Sulfur switches reversibly alter peptide material properties under physiologically relevant conditions.
  • The position of sulfur atoms in side chains significantly impacts polypeptide conformations.
  • Synthetic peptide materials can be triggered by oxidation/reduction, alkylation, and photochemical reactions.

Conclusions:

  • Sulfur switches offer a versatile platform for creating responsive peptide materials.
  • These switches can be tailored by varying sulfur atom location and incorporating synthetic amino acids.
  • Future research should focus on the biological interactions of sulfur-switched peptide materials.