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Related Concept Videos

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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DNA probes are fragments of DNA labeled with a reporter tag to enable their detection or purification. The resulting labeled DNA probes can then hybridize to target nucleic acid sequences through complementary base-pairing, and may be used to recover or identify these regions.
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Structure and Nomenclature of Thiols and Sulfides02:17

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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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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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A highly selective sulfinate ester probe for thiol bioimaging.

Satish R Malwal1, Ajay Labade, Abhijeet S Andhalkar

  • 1Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan Pune 411 008, Maharashtra, India. harinath@iiserpune.ac.in.

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Summary

Sulfinate esters exhibit selective reactivity with thiols at physiological pH. This discovery enabled the development of a novel optical probe for thiol bioimaging.

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Area of Science:

  • Organic Chemistry
  • Chemical Biology
  • Biomedical Imaging

Background:

  • The sulfinate ester functional group's reactivity remains largely unexplored.
  • Selective chemical transformations are crucial for developing biological probes.

Purpose of the Study:

  • To investigate the unexplored chemistry of sulfinate esters.
  • To develop a novel optical probe for thiol detection and bioimaging.

Main Methods:

  • Investigated the reaction of sulfinate esters with various nucleophiles.
  • Characterized the selectivity of the reaction towards thiols at physiological pH.
  • Synthesized and validated an optical probe utilizing the sulfinate ester linkage.

Main Results:

  • Demonstrated that sulfinate esters undergo highly selective nucleophilic substitution by thiols.
  • Established the reaction proceeds efficiently at physiological pH.
  • Developed a functional optical probe for sensitive thiol bioimaging.

Conclusions:

  • The sulfinate ester functional group possesses unique and selective reactivity towards thiols.
  • This chemistry provides a versatile and cleavable trigger for probe development.
  • The developed optical probe is suitable for advanced thiol bioimaging applications.