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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
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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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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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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Sulfur Assimilation01:20

Sulfur Assimilation

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Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to...
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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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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.
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Drug Metabolism: Phase II Reactions01:14

Drug Metabolism: Phase II Reactions

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Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Decarboxylative sulfation by persulfates.

Zhen Xia1,2, Ting Deng1, Chunlan Song1

  • 1State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering, Hunan University Changsha 410082 China jkli@hnu.edu.cn.

Chemical Science
|June 2, 2025
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Summary
This summary is machine-generated.

This study introduces a novel radical reaction for synthesizing organosulfates directly from carboxylic acids using persulfates. This method offers a versatile alternative to traditional O-sulfonation, expanding synthetic possibilities.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Traditional O-sulfonation is limited to hydroxyl-containing compounds.
  • A new disconnection strategy for organosulfate synthesis is needed.
  • Organosulfates can serve as isosteres to improve metabolic profiles.

Purpose of the Study:

  • To develop a direct decarboxylative sulfation method for organosulfate synthesis.
  • To explore the use of persulfates as both oxidants and sulfate sources.
  • To enable the replacement of carboxylic acids with organosulfate groups.

Main Methods:

  • A radical-mediated decarboxylative sulfation reaction was developed.
  • Persulfates were utilized as a dual-acting reagent (oxidant and O-O source).
  • The reaction proceeds via C-O bond formation and C-OSO3- bond formation.

Main Results:

  • Direct synthesis of organosulfates from diverse carboxylic acids was achieved.
  • The method overcomes limitations of traditional O-sulfonation.
  • Persulfates efficiently generate carbon-centered radicals and facilitate sulfation.

Conclusions:

  • A novel and versatile method for organosulfate synthesis via direct decarboxylative sulfation has been established.
  • This approach broadens the scope of organosulfate preparation.
  • The synthesized organosulfates hold potential as isosteres for drug discovery.