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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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The glycocalyx is a carbohydrate-rich, fuzzy-appearing layer on the outer surface of the cell membrane. It is highly hydrophilic, because of this it attracts large amounts of water to the cell's surface. This aids the cell's interaction with the watery environment and also helps it to obtain substances dissolved in the water. It is also important for cell identification, self/non-self determination, and embryonic development and is used in cell-to-cell attachments to form tissues.
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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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Diversity-oriented synthesis of glycomimetics.

Michael Meanwell1, Gaelen Fehr1, Weiwu Ren1

  • 1Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada.

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Summary

This study introduces a novel one-pot reaction for synthesizing diverse glycomimetic building blocks. This method simplifies the creation of complex carbohydrate mimics for drug discovery.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Carbohydrate Chemistry

Background:

  • Glycomimetics are crucial therapeutic leads due to their structural mimicry of natural carbohydrates.
  • The complexity of glycomimetics hinders traditional synthesis and library generation.
  • Developing efficient methods for glycomimetic synthesis is vital for drug discovery.

Purpose of the Study:

  • To develop a streamlined, one-pot method for synthesizing stereochemically defined glycomimetic building blocks.
  • To explore the utility of this method for generating diverse libraries of glycomimetics.
  • To elucidate the stereochemical control mechanisms in the reaction.

Main Methods:

  • A one-pot proline-catalyzed aldehyde α-functionalization/aldol reaction.
  • Density functional theory (DFT) calculations to analyze diastereoselectivity.
  • Synthesis of various glycomimetic classes including iminosugars and nucleoside analogues.

Main Results:

  • Successfully produced a range of glycomimetic building blocks with diverse functional groups (fluoro, chloro, bromo, trifluoromethylthio, azodicarboxylate).
  • Demonstrated high stereochemical control in the dynamic kinetic resolution process.
  • DFT calculations revealed key steric and electrostatic interactions governing diastereoselectivity.
  • Rapidly generated diverse libraries of iminosugars, nucleoside analogues, carbasugars, and carbohydrates from common intermediates.

Conclusions:

  • The developed one-pot reaction offers a powerful and efficient strategy for glycomimetic synthesis.
  • This method overcomes limitations of traditional approaches, enabling rapid library generation.
  • The findings facilitate the discovery of novel carbohydrate-based therapeutics.