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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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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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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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Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
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Protection of Alcohols02:31

Protection of Alcohols

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This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
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Surface Membrane Barriers01:18

Surface Membrane Barriers

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The skin and mucous membranes serve as the primary line of defense against pathogens by providing both physical and chemical protection. These barriers are essential in preventing the entry and establishment of microbes, thereby maintaining the integrity of the host.
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Updated: Mar 31, 2026

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation
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The versatile low-molecular-weight thiols: Beyond cell protection.

Min Wang1, Qunfei Zhao1, Wen Liu1,2

  • 1State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China.

Bioessays : News and Reviews in Molecular, Cellular and Developmental Biology
|October 31, 2015
PubMed
Summary

Low-molecular-weight thiols, including mycothiol (MSH) and ergothioneine (EGT), are crucial for cellular defense and natural product biosynthesis. Their roles in producing compounds like lincomycin A highlight diverse enzymatic functions beyond redox maintenance.

Keywords:
ergothioneinelow-molecular-weight thiolsmycothiolnon-Leloir pathwaysulfur incorporationthiolation carrier

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Area of Science:

  • Biochemistry
  • Natural Product Synthesis
  • Cellular Biology

Background:

  • Low-molecular-weight (LMW) thiols are vital for maintaining cellular redox balance and protecting against reactive species.
  • Their involvement in complex biosynthetic pathways, particularly for natural products, remains underexplored.
  • Mycothiol (MSH) and ergothioneine (EGT) are key LMW thiols with established cellular roles.

Purpose of the Study:

  • To investigate the role of LMW thiols, specifically MSH and EGT, in the biosynthesis of natural products.
  • To explore the potential functions of EGT as a chiral carrier and activator in glycosylation.
  • To highlight the broader enzymatic activities of LMW thiols beyond cellular protection.

Main Methods:

  • Metabolic pathway analysis
  • Enzymatic assays
  • Literature review of thiol-dependent enzymes

Main Results:

  • The metabolic coupling of MSH and EGT was found to program the biosynthesis of lincomycin A.
  • Ergothioneine (EGT) is hypothesized to act as a chiral thiolation carrier and a novel sugar activator for glycosylation.
  • Evidence suggests LMW thiols, including MSH, serve as sulfur donors in the synthesis of sulfur-containing natural products.

Conclusions:

  • LMW thiols possess diverse biological activities extending beyond their known roles in redox homeostasis.
  • The constructive role of thiols in natural product biosynthesis warrants further investigation.
  • Understanding thiol-dependent enzymes is crucial for uncovering novel biosynthetic pathways and functions.