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Preparation and Reactions of Sulfides02:26

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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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Rapid methods for high-throughput detection of sulfoxides.

Janna Shainsky1, Netta-Lee Derry, Yael Leichtmann-Bardoogo

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Developing rapid, high-throughput screening methods is crucial for identifying efficient biocatalysts for enantiopure sulfoxide synthesis. This study presents four detection methods, three optimized for screening, aiding the discovery of novel biocatalysts for chiral sulfoxide production.

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Area of Science:

  • Biocatalysis and Enzyme Engineering
  • Organic Synthesis
  • Chiral Chemistry

Background:

  • Enantiopure sulfoxides are vital in pharmaceuticals and as chiral auxiliaries.
  • Biocatalytic enantioselective oxidation of prochiral sulfides offers an economical route to optically pure sulfoxides.
  • Efficient high-throughput screening (HTS) methods are essential for identifying suitable biocatalysts.

Purpose of the Study:

  • To develop and evaluate four distinct methods for detecting sulfoxides produced via whole-cell biocatalysis.
  • To adapt three of these methods for high-throughput screening (HTS) to accelerate biocatalyst discovery.
  • To identify novel biocatalysts for the enantioselective synthesis of chiral sulfoxides.

Main Methods:

  • Four sulfoxide detection methods were assessed: fluorescence (omeprazole-based), iodine release via reduction, selective enzyme inhibition (horse liver alcohol dehydrogenase), and colorimetric adrenochrome detection.
  • Three methods were optimized for HTS, including adapting an iodine release assay using solvent-resistant plates.
  • A saturation mutagenesis library of toluene ortho-monooxygenase was screened using the enzyme inhibition method with methyl-p-tolyl sulfide.

Main Results:

  • The omeprazole fluorescence method showed potential for HTS but did not yield active variants.
  • The iodine release method was successfully adapted for HTS.
  • The enzyme inhibition method achieved an 89% success rate, identifying two new active mutants.
  • The adrenochrome method proved useful only for qualitative detection due to low sensitivity in whole-cell screening.

Conclusions:

  • The study presents simple, inexpensive, and equipment-light sulfoxide detection methods suitable for HTS.
  • The developed HTS methods facilitate the discovery and optimization of biocatalysts for enantiopure sulfoxide synthesis.
  • The selective enzyme inhibition method proved effective for screening mutant libraries, yielding promising results.