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Related Concept Videos

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.
Glycosylation occurs in...
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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.
Multiple sugar molecules that may or may...
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Formation of Lipopolysaccharides01:19

Formation of Lipopolysaccharides

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Lipopolysaccharides (LPS) are crucial components of the outer membrane of Gram-negative bacteria, serving both structural and functional roles. It contributes to membrane stability and protects bacteria from host immune responses. LPS is composed of three major regions—lipid A, a core oligosaccharide, and an O antigen. The biosynthesis and assembly of LPS involve a highly coordinated set of enzymatic reactions and transport mechanisms. Additionally, LPS is recognized as an endotoxin,...
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Proteoglycans01:05

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Glycans, a class of complex heterogeneous molecules, can be covalently attached to proteins to form glycosylated proteins that regulate various physiological and pathological processes. Glycosylated proteins or glycoproteins comprise N-linked and O-linked oligosaccharides. O-glycosylation is the most common type of protein glycosylation. Here, glycans attach to the oxygen atom of the hydroxyl groups of Serine or Threonine residues. O-linked glycosylation occurs later in protein processing,...
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Preparation of Carboxylic Acids: Overview01:31

Preparation of Carboxylic Acids: Overview

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There are various methods for the preparation of carboxylic acids. For example, oxidation of primary alcohols or aldehydes using strong oxidizing agents results in a carboxylic acid.  Aldehydes can also be oxidized in the presence of mild oxidizing agents.
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C–C Bond Formation: Aldol Condensation Overview01:10

C–C Bond Formation: Aldol Condensation Overview

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Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
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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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Guidelines for O-Glycoside Formation from First Principles.

Peter R Andreana1, David Crich2,3,4

  • 1Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States.

ACS Central Science
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Summary

This study outlines 12 key guidelines to simplify and improve the reproducibility of glycosylation reactions. Following these recommendations for concentration, temperature, and counterions can enhance experimental outcomes.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis

Background:

  • Glycosylation reactions are crucial in synthesizing complex carbohydrates but suffer from significant complexity and poor reproducibility.
  • Developing standardized protocols is essential for advancing carbohydrate-based research and drug discovery.

Discussion:

  • This work presents 12 practical guidelines focusing on critical reaction parameters: concentration, temperature, and counterions.
  • These guidelines aim to demystify glycosylation procedures and provide a framework for consistent results.

Key Insights:

  • Optimizing concentration, temperature, and counterion selection directly impacts glycosylation efficiency and stereoselectivity.
  • Adherence to these guidelines can substantially reduce experimental variability and troubleshooting time.

Outlook:

  • Implementation of these guidelines is expected to accelerate the development of novel glycoconjugates and carbohydrate-based therapeutics.
  • Further research may explore the application of these principles to a broader range of glycosylation methodologies.