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Related Concept Videos

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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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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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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Drug Metabolism: Phase II Reactions01:14

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Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
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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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Amines to Sulfonamides: The Hinsberg Test01:23

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The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
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H2SO4 and SO3 transfer reactions in a sulfopeptide-basic peptide complex.

Amanda L Patrick1, Nicolas C Polfer1

  • 1Department of Chemistry, University of Florida , P.O. Box 117200, Gainesville, Florida 32611, United States.

Analytical Chemistry
|September 4, 2015
PubMed
Summary

Sulfur trioxide and sulfuric acid can transfer between peptides. This study demonstrates intermolecular sulfo-group transfer between peptides using collisional activation, impacting proteomics and post-translational modification discovery.

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Area of Science:

  • Analytical Chemistry
  • Biochemistry
  • Mass Spectrometry

Background:

  • Sulfonation is a crucial post-translational modification.
  • Understanding the mechanisms of sulfonylation is vital for proteomics.

Purpose of the Study:

  • To investigate the intermolecular transfer of sulfo-groups between peptides.
  • To characterize the products of sulfo-group transfer reactions.

Main Methods:

  • Formation of noncovalent complexes between an acidic sulfopeptide (sSE) and a basic peptide (R3).
  • Collisional activation in a quadrupole ion trap to induce intermolecular transfer.
  • Mass spectrometry (MS3) experiments for product ion characterization.
  • Isotope labeling and energy-resolved collision-induced dissociation (CID) for peak assignment validation.

Main Results:

  • Demonstrated intermolecular transfer of sulfuric acid (H2SO4) and sulfur trioxide (SO3) from sSE to R3.
  • Identified and characterized the resulting sulfo-group transferred peptide ions.
  • Confirmed reaction pathways through MS3 and CID experiments.

Conclusions:

  • Intermolecular sulfo-group transfer between peptides is feasible under collisional activation.
  • The findings provide insights into potential mechanisms of sulfonylation in biological systems.
  • This work has implications for developing new strategies in proteomics and post-translational modification discovery.