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Related Concept Videos

Protein Glycosylation01:25

Protein Glycosylation

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.
Glycosylation occurs in...
Oligosaccharide Assembly01:24

Oligosaccharide Assembly

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.
Multiple sugar molecules that may or may...
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

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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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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Glycosylation using unprotected alkynyl donors.

Sreeman K Mamidyala1, M G Finn

  • 1Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, California 92037, USA. sreeman@scripps.edu

The Journal of Organic Chemistry
|October 16, 2009
PubMed
Summary

Gold(III) activation offers an effective method for synthesizing saccharides using propargyl glycosyl donors. This approach allows for efficient glycosylation reactions with various alcohol acceptors, simplifying carbohydrate synthesis.

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Catalysis

Background:

  • Saccharide synthesis is crucial for understanding biological processes and developing therapeutics.
  • Traditional glycosylation methods often require protecting groups, adding steps and complexity.
  • Propargyl glycosyl donors offer a potential alternative due to their unique reactivity.

Purpose of the Study:

  • To investigate the efficacy of Gold(III) chloride (AuCl3) as a catalyst for activating unprotected propargyl glycosyl donors.
  • To explore the scope and limitations of this method with different monosaccharides and alcohol acceptors.
  • To evaluate the influence of donor structure on reactivity and reaction conditions.

Main Methods:

  • Utilized terminal propargyl glycosides of glucose, galactose, and mannose.
  • Employed Gold(III) chloride (5% loading) in acetonitrile under reflux conditions.
  • Reacted donors with primary and secondary alcohol acceptors in varying molar ratios.

Main Results:

  • Gold(III) effectively catalyzed the activation of unprotected propargyl glycosyl donors for saccharide synthesis.
  • Donors with a 2-butynyl group exhibited enhanced reactivity, yielding products at lower temperatures.
  • Primary alcohols were efficient acceptors; secondary alcohols showed diminished reactivity.

Conclusions:

  • Gold(III)-catalyzed activation of propargyl glycosyl donors provides a convenient and effective route to saccharides.
  • The propargylic donor system is advantageous due to ease of preparation, scalability, and storage stability.
  • This method simplifies glycosylation by avoiding the need for protecting groups on the donors.