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Related Concept Videos

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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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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Phosphodiester Linkages01:01

Phosphodiester Linkages

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Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
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Oligosaccharide Assembly01:24

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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
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Protein Glycosylation01:25

Protein Glycosylation

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Glycosylation, the most common post-translational modification for proteins, serves diverse functions. Adding sugars to proteins makes the proteins more resistant to proteolytic digestion. Glycosylated proteins can act as markers and receptors to promote cell-cell adhesion. Additionally, they have many essential quality control functions in the cell, such as correct protein folding and facilitating transport of misfolded proteins to the cytosol, which can be degraded.
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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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Glycoconjugates via phosphorus ylides.

Ehsan Gonchepour1, Constantinos G Neochoritis1, Katarzyna Kurpiewska2

  • 1Department of Pharmacy, Drug Design group, University of Groningen, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.

European Journal of Organic Chemistry
|September 1, 2020
PubMed
Summary

Researchers developed a straightforward method to create rare chimeric compounds, merging phosphorus ylides and glycosyl formamides. Structural analysis and database mining provide insights for their use in synthesis and drug development.

Keywords:
chemical biologyglycoconjugatesglycosyl formamidesmulti-component reactionsphosphorus ylides

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Area of Science:

  • Organic Chemistry
  • Glycochemistry
  • Medicinal Chemistry

Background:

  • Access to novel chimeric compounds is crucial for synthetic and medicinal chemistry.
  • Phosphorus ylides and glycosyl formamides are valuable building blocks with diverse applications.

Purpose of the Study:

  • To develop an efficient synthetic route to rare chimeric compounds combining phosphorus ylides and glycosyl formamides.
  • To gain structural insights into this novel class of compounds.
  • To explore the potential applications of these derivatives in synthesis and drug discovery.

Main Methods:

  • Facile synthesis yielding complex chimeric compounds.
  • X-ray crystallography for structural determination.
  • Data mining of the Cambridge Structural Database for related compounds.

Main Results:

  • High-yielding synthesis of rare chimeric compounds.
  • Detailed structural elucidation of the synthesized compounds.
  • Identification of potential applications as synthetic intermediates and in medicinal chemistry.

Conclusions:

  • The developed method provides efficient access to valuable chimeric compounds.
  • Structural data enhances understanding of this compound class.
  • These derivatives show promise as versatile synthons and for improving pharmacokinetic properties of bioactive molecules.