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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.
7.8K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.6K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.9K
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,...
5.9K
Redox Titration: Other Oxidizing and Reducing Agents01:26

Redox Titration: Other Oxidizing and Reducing Agents

1.5K
Besides iodine, other oxidizing or reducing agents can serve as titrants in redox titrations. Common oxidizing titrants include KMnO4, cerium(IV), and K2Cr2O7. The choice of oxidizing titrants depends on factors like stability, cost, analyte strength, and reaction rate between the analyte and titrant. KMnO4 is a strong oxidizing titrant that reduces from Mn(VII) to Mn(II) in a highly acidic solution, simultaneously oxidizing the analyte to a higher oxidation state. In this case, KMnO4 acts as a...
1.5K
Effects of EDTA on End-Point Detection Methods01:18

Effects of EDTA on End-Point Detection Methods

723
Different methods, such as visual observance of metal-ion indicators, spectroscopic techniques, and potentiometric methods, can determine the endpoint of an EDTA titration.
In the visual method, metal-ion indicators (metallochromic dyes), which have distinct colors in their free and complex forms, are added to the mixture to signal the titration's end point. They form stable complexes with metal ions, but these complexes are weaker than the corresponding metal–EDTA complexes. As a...
723
Precipitation Titration: Endpoint Detection Methods01:19

Precipitation Titration: Endpoint Detection Methods

6.2K
In argentometric precipitation titrations, endpoints can be detected visually by the Mohr, Volhard, and Fajans methods. In the Mohr method, adding a soluble chromate indicator gives an initial yellow color to the analyte solution. As the titrant is added, the first excess of silver ions forms a red silver chromate precipitate, marking the endpoint. The solution pH should be maintained at about 8 by adding solid CaCO3.
In the Volhard method, a standard excess of AgNO3 is first added to the...
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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

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Thiolate-based dinitrosyl iron complexes: Decomposition and detection and differentiation from S-nitrosothiols.

Agnes Keszler1, Anne R Diers1, Zhen Ding1

  • 1Department of Biophysics and Redox Biology Program, Medical College of Wisconsin, Milwaukee, WI 53226, United States.

Nitric Oxide : Biology and Chemistry
|January 24, 2017
PubMed
Summary

Dinitrosyl iron complexes (DNIC) are stable at neutral pH but decompose with excess thiol. Mercury chloride accelerates DNIC degradation, suggesting overestimation of S-nitrosothiols in diagnostic methods.

Keywords:
DNICNO-dependent chemiluminescenceNitric oxideS-nitrosothiols

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Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation
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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Nitric Oxide Research

Background:

  • Dinitrosyl iron complexes (DNIC) form from Fe(II), nitric oxide (NO), and anions, existing as monomeric and dimeric forms.
  • Thiolate groups are key biological ligands for DNIC formation, which are implicated in NO signaling and iron homeostasis.
  • DNIC are abundant NO-derived products and potential intermediates in S-nitrosothiol synthesis within cells.

Purpose of the Study:

  • To assess the stability of low molecular weight DNIC in aqueous solutions.
  • To investigate the detection challenges of DNIC in the presence of S-nitrosothiols and other NO metabolites.
  • To evaluate the impact of mercury chloride on DNIC stability and its implications for S-nitrosothiol quantification.

Main Methods:

  • Spectrophotometry
  • Electron Paramagnetic Resonance (EPR) spectroscopy
  • Ozone-based chemiluminescence
  • High-Performance Liquid Chromatography (HPLC)
  • Analysis in simple and complex biological systems

Main Results:

  • At neutral pH, dimeric DNIC (bi-DNIC) are stable for hours.
  • Excess thiol leads to DNIC decomposition, producing nitrite and NO, but not S-nitrosothiols.
  • Mercury chloride significantly accelerates DNIC degradation.

Conclusions:

  • DNIC stability is pH-dependent and influenced by thiol concentration.
  • The use of mercury chloride in S-nitrosothiol detection methods may lead to overestimation of S-nitrosothiol levels.
  • Re-evaluation of diagnostic methods employing mercury chloride for S-nitrosothiol quantification is warranted.