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Related Concept Videos

Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

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, similar...
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.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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.
Phase II Reactions: Miscellaneous Conjugation Reactions01:19

Phase II Reactions: Miscellaneous Conjugation Reactions

Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...
Sulfur Assimilation01:20

Sulfur Assimilation

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 become...

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Related Experiment Video

Updated: Jul 1, 2026

Detection of Nitric Oxide and Superoxide Radical Anion by Electron Paramagnetic Resonance Spectroscopy from Cells using Spin Traps
13:21

Detection of Nitric Oxide and Superoxide Radical Anion by Electron Paramagnetic Resonance Spectroscopy from Cells using Spin Traps

Published on: August 18, 2012

Direct NO group transfer from S-nitrosothiols to iron centres.

A R Butler1, S Elkins-Daukes, D Parkin

  • 1Department of Chemistry, University of St. Andrews, St. Andrews, Fife, UK KY16 9ST.

Chemical Communications (Cambridge, England)
|September 21, 2002
PubMed
Summary

S-nitrosothiols rapidly transfer NO groups to iron centers in DMPS and MGD complexes. This reaction mechanism is crucial for understanding nitrosothiol chemistry and iron interactions.

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Application of Genetically Encoded Fluorescent Nitric Oxide (NO•) Probes, the geNOps, for Real-time Imaging of NO• Signals in Single Cells
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Application of Genetically Encoded Fluorescent Nitric Oxide (NO•) Probes, the geNOps, for Real-time Imaging of NO• Signals in Single Cells

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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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Last Updated: Jul 1, 2026

Detection of Nitric Oxide and Superoxide Radical Anion by Electron Paramagnetic Resonance Spectroscopy from Cells using Spin Traps
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Published on: August 18, 2012

Application of Genetically Encoded Fluorescent Nitric Oxide (NO•) Probes, the geNOps, for Real-time Imaging of NO• Signals in Single Cells
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Application of Genetically Encoded Fluorescent Nitric Oxide (NO•) Probes, the geNOps, for Real-time Imaging of NO• Signals in Single Cells

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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
08:23

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

Published on: February 16, 2022

Area of Science:

  • Bioinorganic Chemistry
  • Coordination Chemistry
  • Chemical Biology

Background:

  • S-nitrosothiols (RSNOs) are important signaling molecules involved in various physiological processes.
  • Iron-sulfur complexes play critical roles in biological systems, including electron transfer and enzyme catalysis.
  • Understanding the reactivity of RSNOs with metal centers is key to elucidating their biological functions.

Purpose of the Study:

  • To investigate the reaction mechanism between S-nitrosothiols and specific Fe(II) complexes.
  • To determine the fate of the NO group during the reaction with iron centers.
  • To explore the potential of DMPS and MGD as ligands for iron in the context of nitrosothiol interactions.

Main Methods:

  • Spectroscopic analysis to monitor reaction progress.
  • Kinetic studies to determine reaction rates.
  • Characterization of reaction products.

Main Results:

  • S-nitrosothiols were observed to react rapidly with Fe(II) complexes of 2,3-dimercapto-1-propanesulfonic acid (DMPS) and N-methyl-D-glucamine dithiocarbamate (MGD).
  • The NO group was directly transferred to the iron centers of these complexes.
  • The reaction kinetics were found to be dependent on the specific S-nitrosothiol and the iron complex used.

Conclusions:

  • The study demonstrates a direct NO group transfer from S-nitrosothiols to Fe(II) centers coordinated by DMPS and MGD.
  • This finding provides insight into the chemical reactivity of S-nitrosothiols and their interactions with biological metal ions.
  • The results suggest potential implications for the biological activity and therapeutic applications of S-nitrosothiols and their metal complexes.