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Related Concept Videos

Conjugate Addition of Enolates: Michael Addition01:08

Conjugate Addition of Enolates: Michael Addition

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The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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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.
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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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.
5.3K
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)01:27

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

3.7K
α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are...
3.7K
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

582
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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Related Experiment Video

Updated: Oct 30, 2025

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

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A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition.

Junyi Chen1, Xutao Ma1, Kevin J Edgar2

  • 1College of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.

Polymers
|July 2, 2021
PubMed
Summary
This summary is machine-generated.

Researchers developed a versatile method to create functional polysaccharide conjugates using thiol-Michael addition. These novel materials show promise for biomedical applications, including antimicrobial activity and drug delivery.

Keywords:
cationic polysaccharidepolysaccharide chemical modificationthiol-Michael addition

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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biomedical Engineering

Background:

  • Polysaccharide conjugates are valuable renewable materials with potential for drug delivery and charge modification.
  • Tailoring polysaccharide properties is crucial for advanced biomedical applications.

Purpose of the Study:

  • To develop a simple, efficient, and versatile method for synthesizing functional polysaccharide conjugates.
  • To explore the potential of these conjugates in biomedical applications, particularly antimicrobial activity.

Main Methods:

  • Hydroxypropyl cellulose (HPC) and dextran (Dex) were methacrylated to introduce α,β-unsaturated esters.
  • Thiol-Michael addition reactions were employed using various thiols (e.g., 2-thioethylamine, cysteine, quaternary ammonium salt).
  • The click-like reaction was performed in water, offering advantages like speed and high conversion.

Main Results:

  • Functionalized polysaccharide conjugates were successfully synthesized with tunable degrees of substitution (DS).
  • Conjugates bearing quaternary ammonium salts demonstrated significant antimicrobial performance.
  • Minimum inhibitory concentration (MIC) studies and SEM characterization supported the antimicrobial findings.

Conclusions:

  • The thiol-Michael addition offers a modular and efficient route to diverse polysaccharide conjugates.
  • This methodology enables the creation of materials for antimicrobial applications, gene/drug delivery, and biomimicry.
  • The developed polysaccharide conjugates represent promising candidates for advanced biomedical solutions.