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Related Concept Videos

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Phase II Conjugation Reactions: Overview01:14

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Conjugation, a key component of phase II biotransformation reactions, is a vital process in drug detoxification. It involves transferring endogenous substances like glucuronic acid, sulfate, and glycine to drugs or their metabolites formed in phase I reactions. These conjugation reactions, often catalyzed by specific enzymes, transform potentially harmful metabolites into inactive, water-soluble forms easily excreted in urine or bile. By enhancing polarity and eliminating pharmacological...
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Phase II Reactions: Miscellaneous Conjugation Reactions01:19

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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...
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Phase II Reactions: Glutathione Conjugation and Mercapturic Acid Formation01:22

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Glutathione, a tripeptide made up of glutamate, cysteine, and glycine, is a critical player in the detoxification of drugs and xenobiotics via a process known as glutathione conjugation or mercapturic acid formation. This phase II biotransformation reaction involves the covalent binding of glutathione to a drug or its metabolite, enhancing the compound's water solubility and enabling its excretion.
Several distinctive characteristics distinguish glutathione conjugation from other phase II...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Palladium/Photoredox-Catalyzed Three-Component Coupling for Glycoconjugation.

Lifan Deng1,2,3, Ao Shen1, Siyu Zhang1

  • 1Department of Nuclear Medicine, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University, and School of Chemical Engineering, Sichuan University, Chengdu, China.

Angewandte Chemie (International Ed. in English)
|April 14, 2026
PubMed
Summary

This study introduces a novel visible-light-driven method for glycoconjugation, using palladium catalysis to efficiently create complex sugar-containing molecules. This approach overcomes previous synthetic challenges in attaching sugar moieties to various targets.

Keywords:
glycoconjugationpalladiumphotoredox‐catalysisradical reactions

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Catalysis

Background:

  • Glycoconjugation is vital for modulating biological functions but is synthetically challenging due to complex carbohydrate structures.
  • Palladium-catalyzed allylic substitution is a powerful synthetic tool, yet its application in glycoconjugation is limited.

Purpose of the Study:

  • To develop an efficient and versatile method for synthesizing complex glycoconjugates.
  • To explore the use of palladium-catalyzed allylic substitution in glycoconjugation reactions.

Main Methods:

  • A visible-light-driven, three-component coupling reaction was developed.
  • The protocol utilizes ortho-iodobiphenyl S-glycosides as glycosyl donors and a Pd(0) catalyst.
  • Glycosyl radical intermediates are generated and coupled with 1,3-butadiene and nucleophiles.

Main Results:

  • The method successfully assembles elaborate glycoconjugates from readily accessible starting materials.
  • The palladium catalyst plays a dual role in generating glycosyl radicals and forming allyl-Pd electrophiles.
  • The reaction demonstrates broad functional-group compatibility, enabling late-stage modifications.

Conclusions:

  • A novel strategy for Pd-catalyzed allylic substitution in glycoconjugation was established.
  • The developed protocol offers a powerful approach for synthesizing diverse glycoconjugates.
  • The method facilitates the modification of complex biomolecules like oligopeptides and small molecules.