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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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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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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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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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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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A Sensitive Visual Method for the Detection of Hydrogen Sulfide Producing Bacteria
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Activatable Small-Molecule Hydrogen Sulfide Donors.

Carolyn M Levinn1, Matthew M Cerda1, Michael D Pluth1

  • 1Department of Chemistry and Biochemistry, Materials Science Institute, Institute of Molecular Biology, University of Oregon, Eugene, Oregon.

Antioxidants & Redox Signaling
|September 27, 2019
PubMed
Summary
This summary is machine-generated.

Hydrogen sulfide (H2S) donors are crucial tools for biological research and drug development. New donors are needed to target specific stimuli and understand H2S release kinetics for therapeutic applications.

Keywords:
carbonyl sulfidehydrogen sulfidereactive sulfur speciessmall molecule donors

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Area of Science:

  • Biochemistry
  • Pharmacology
  • Chemical Biology

Background:

  • Hydrogen sulfide (H2S) is a vital signaling molecule in numerous physiological processes.
  • Developing methods to control H2S release under physiological conditions is essential for research and therapeutic applications.

Purpose of the Study:

  • To review the landscape of small-molecule H2S donors.
  • To highlight the need for novel donors with specific stimuli-responsiveness and well-defined control compounds.
  • To discuss the importance of understanding H2S release kinetics.

Main Methods:

  • Review of existing literature on small-molecule H2S donors.
  • Categorization of donors based on activation mechanisms (hydrolysis, endogenous species, external stimuli).
  • Discussion of carbonyl sulfide (COS) as an alternative H2S source.

Main Results:

  • A wide array of H2S donors have been developed, responding to diverse triggers like hydrolysis, thiols, ROS, enzymes, photoactivation, and bio-orthogonal chemistry.
  • Carbonyl sulfide (COS) hydrolysis catalyzed by carbonic anhydrase offers an alternative route to H2S generation.
  • Existing donors serve as valuable tools for biological investigation and therapeutic development.

Conclusions:

  • Small-molecule H2S donors are indispensable chemical tools for biological research and pharmacological interventions.
  • Future development should focus on stimuli-specific donors and precise control compounds to isolate H2S effects.
  • Further research is required to elucidate the impact of varying H2S release rates (rapid vs. gradual) in biological systems.