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Related Concept Videos

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...
Biosynthesis of Polysaccharides01:26

Biosynthesis of Polysaccharides

Polysaccharides such as glycogen and starch are synthesized from nucleoside diphosphate sugars, primarily uridine diphosphate glucose (UDPG) and adenosine diphosphate glucose (ADPG). These activated glucose donors act as key intermediates in carbohydrate metabolism and biosynthesis. UDPG primarily involves glycogen synthesis in animals and many bacteria, while ADPG plays a fundamental role in starch synthesis in plants and certain bacteria.UDPG is formed when glucose-1-phosphate reacts with...
Protein Modifications in the RER01:26

Protein Modifications in the RER

Modification of secretory and transmembrane proteins entering the rough ER begins in the ER lumen. These modifications aid in protein folding and stabilize the acquired tertiary structure. Protein modifications in the rough ER co-occur at different stages of protein folding.
Broadly, these modifications can be categorized into four main categories — glycosylation, formation of disulfide bonds, assembly of protein subunits, and specific proteolytic cleavages like removal of signal sequences.
Proteoglycans01:05

Proteoglycans

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,...
Membrane Carbohydrates01:30

Membrane Carbohydrates

The plasma membrane is a dynamic barrier composed of lipids, proteins, and carbohydrates. It is the epicenter of many cellular processes required for cell growth and survival. Carbohydrates have unique structural and chemical properties that help the plasma membrane to carry out its functions effectively.
Membrane carbohydrates do not have any hydrophobic region and are exclusively located on the cell's outer surface. The addition of sugar molecules or glycosylation of proteins happens in...
Protein Folding Quality Check in the RER01:29

Protein Folding Quality Check in the RER

ER is the primary site for the maturation and folding of soluble and transmembrane secretory proteins. The calnexin cycle is a specific chaperone system that folds and assesses the confirmation of N-glycosylated proteins before they can exit the ER lumen. The primary players of this quality check pipeline are the lectins, ER-resident chaperones, and a glucosyl transferase enzyme. In case the calnexin system in the lumen fails to salvage a misfolded protein, it is transported to the cytoplasm...

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Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
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Published on: November 25, 2017

β-Rhamnosides from 6-thio mannosides.

Alphert E Christina1, Daan van der Es, Jasper Dinkelaar

  • 1Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.

Chemical Communications (Cambridge, England)
|February 7, 2012
PubMed
Summary
This summary is machine-generated.

This study demonstrates a stereoselective synthesis of 1,2-cis rhamnosides using 6-thio-6-deoxy-mannosyl donors. The method involves condensation and subsequent reductive removal of the thio functionality, yielding the desired products with high selectivity.

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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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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Stereoselective Reactions

Background:

  • Stereoselective synthesis of carbohydrates is crucial for developing novel therapeutics and understanding biological processes.
  • 1,2-cis-glycosides are challenging to synthesize due to inherent stereochemical preferences.
  • 6-thio-6-deoxy-mannosyl donors offer a unique approach to controlling glycosylation stereochemistry.

Purpose of the Study:

  • To develop a highly stereoselective method for synthesizing 1,2-cis rhamnosides.
  • To investigate the mechanism underlying the observed 1,2-cis-selectivity in glycosylation reactions.
  • To provide a reliable route to valuable carbohydrate structures.

Main Methods:

  • Condensation of 6-thio-6-deoxy-mannosyl donors.
  • Stereoselective glycosylation reactions.
  • Reductive removal of the 6-thio group using reagents such as Raney nickel.

Main Results:

  • High stereoselectivity for the formation of 1,2-cis products during the condensation of modified mannosyl donors.
  • Successful synthesis of 1,2-cis rhamnosides via reductive desulfurization.
  • Identification of a proposed oxocarbenium intermediate in equilibrium with a bridged sulfonium ion, explaining the observed stereochemical outcome.

Conclusions:

  • The use of 6-thio-6-deoxy-mannosyl donors provides an effective strategy for achieving high 1,2-cis selectivity in glycosylation.
  • The synthetic route is efficient for accessing 1,2-cis rhamnosides.
  • The mechanistic insights support a model involving oxocarbenium and sulfonium intermediates in controlling stereochemistry.