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Related Concept Videos

Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

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Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
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Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
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Protection of Alcohols02:31

Protection of Alcohols

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This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

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The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the...
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Phase II Conjugation Reactions: Overview01:14

Phase II Conjugation Reactions: Overview

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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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Related Experiment Video

Updated: Sep 18, 2025

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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A Mild Protecting-Group Free Strategy for Neoglycoconjugate Synthesis.

Princey Raju1, Chunhua Dong2, Craig R Garen2

  • 1Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.

Bioconjugate Chemistry
|June 23, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a new method for creating neoglycoconjugates without protecting sugars. This approach uses mild conditions and thiol-ene coupling (TEC) for attaching glycans to sensitive proteins.

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Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
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Area of Science:

  • Carbohydrate Chemistry
  • Chemical Biology
  • Bioconjugation

Background:

  • Neoglycoconjugates are vital tools for research and therapeutics, mimicking natural structures.
  • Conventional synthesis methods often require harsh conditions incompatible with sensitive proteins.
  • Developing mild, efficient conjugation strategies is crucial for advancing glycoconjugate applications.

Purpose of the Study:

  • To develop a simple, modular, and chemoselective strategy for synthesizing neoglycoconjugates.
  • To enable glycan conjugation under mild conditions, avoiding protecting groups.
  • To facilitate the preparation of neoglycoconjugates for sensitive or aggregation-prone proteins.

Main Methods:

  • A novel chemoselective coupling between unprotected sugars and hydroxylamines under mild acidic conditions.
  • Utilizing a terminal alkene as a handle for subsequent conjugation via thiol-ene coupling (TEC).
  • Optimization of TEC conditions using various photocatalysts for efficient protein conjugation.

Main Results:

  • Successful synthesis of neoglycoconjugates from unprotected N- and O-linked glycans.
  • Demonstration of facile protein conjugation using TEC with diverse photocatalysts.
  • Application of the method to an aggregation-prone protein, α-synuclein, under mild conditions.

Conclusions:

  • The developed strategy offers a protecting-group-free approach for neoglycoconjugate synthesis.
  • This method is compatible with sensitive proteins and various glycan types.
  • It provides a versatile platform for creating tailored glycoconjugates for biological studies and therapeutic development.