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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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.
EDTA: Auxiliary Complexing Reagents01:26

EDTA: Auxiliary Complexing Reagents

EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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.
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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,...

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Thioester hydrolysis promoted by a mononuclear zinc complex.

James J Danford1, Atta M Arif, Lisa M Berreau

  • 1Department of Chemistry and Biochemistry, Utah State University, Logan, Utah 84322-0300, USA.

Inorganic Chemistry
|December 31, 2009
PubMed
Summary

A zinc complex catalyzes thioester hydrolysis, mimicking human glyoxalase II activity. This reaction yields thiol products, offering insights into biological detoxification mechanisms.

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Area of Science:

  • Bioinorganic Chemistry
  • Enzyme Mimicry
  • Organic Reaction Mechanisms

Background:

  • Human glyoxalase II is a crucial enzyme in detoxification pathways, utilizing a binuclear metal center.
  • Understanding the catalytic mechanisms of related monozinc complexes can provide insights into glyoxalase II function.
  • Thioester hydrolysis is a key reaction in various biological and chemical processes.

Purpose of the Study:

  • To investigate the catalytic activity of a mononuclear zinc complex in thioester hydrolysis.
  • To explore the reaction mechanism and kinetics of zinc-promoted thioester cleavage.
  • To establish a model system for studying the monozinc-containing form of human glyoxalase II.

Main Methods:

  • Synthesis and characterization of the mononuclear zinc complex [(bpta)Zn](ClO(4))(2).0.5H(2)O.
  • Hydrolysis of the deuterated thioester PhCH(OH)C(O)SCD(3) in a CH(3)CN:H(2)O solvent mixture.
  • Kinetic analysis of the reaction products, including CD(3)SH and zinc thiolate intermediates.
  • Determination of activation energy for the hydrolysis reaction.

Main Results:

  • The zinc complex effectively promoted the hydrolysis of the thioester.
  • The reaction produced CD(3)SH and a zinc thiolate complex, which could be further protonated to release more CD(3)SH.
  • Kinetic studies indicated an overall second-order reaction.
  • The activation energy was comparable to that of hydroxide-promoted thioester hydrolysis.

Conclusions:

  • The mononuclear zinc complex serves as a functional model for the monozinc-containing form of human glyoxalase II.
  • This study provides the first investigation into the chemistry relevant to the monozinc form of glyoxalase II.
  • The findings contribute to understanding the catalytic mechanisms of zinc-dependent enzymes involved in detoxification.