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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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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

5.5K
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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.2K
Hydrogen Bonds00:26

Hydrogen Bonds

129.5K
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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Esterase-sensitive trithiane-based hydrogen sulfide donors.

Clovis Shyaka1, Ming Xian, Chung-Min Park

  • 1Department of Chemistry, Gangneung-Wonju National University, Gangneung, Gangwon 25457, South Korea. parkc@gwnu.ac.kr.

Organic & Biomolecular Chemistry
|November 22, 2019
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Summary

New 1,3,5-trithiane donors release hydrogen sulfide (H2S) through enzymatic hydrolysis. The H2S release is controllable and depends on the number of ester bonds, offering a promising approach for H2S delivery.

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Drug Delivery

Background:

  • Hydrogen sulfide (H2S) is a crucial signaling molecule with therapeutic potential.
  • Developing controllable H2S donors is essential for its effective application.
  • Enzymatic hydrolysis offers a targeted approach for drug release.

Purpose of the Study:

  • To develop novel 1,3,5-trithiane-based compounds as enzyme-sensitive hydrogen sulfide (H2S) donors.
  • To investigate the relationship between the structure of these donors and the rate of H2S release.
  • To demonstrate controllable H2S release in the presence of esterase enzymes.

Main Methods:

  • Synthesis of 1,3,5-trithiane derivatives functionalized with esterase-sensitive ester groups.
  • Enzymatic hydrolysis studies using esterase enzymes.
  • Quantification of released hydrogen sulfide (H2S).

Main Results:

  • Successfully synthesized 1,3,5-trithiane functionalized with esterase-sensitive ester groups.
  • Demonstrated that the amount of H2S released is directly dependent on the number of ester bonds present.
  • Showcased controllable H2S release mediated by enzymatic activity.

Conclusions:

  • The developed 1,3,5-trithiane derivatives are effective enzymatic hydrolysis-based hydrogen sulfide (H2S) donors.
  • The rate of H2S release can be tuned by modifying the number of ester linkages.
  • These compounds represent a promising platform for controlled H2S delivery in biological systems.