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Related Concept Videos

Oligosaccharide Assembly01:24

Oligosaccharide Assembly

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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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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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One-Pot Relay Glycosylation.

Xiong Xiao1, Jing Zeng1, Jing Fang1

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A new one-pot relay glycosylation method efficiently forms two glycosidic bonds using a single activator. This approach simplifies complex oligosaccharide synthesis, enabling rapid access to natural products.

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Synthetic Chemistry

Background:

  • Oligosaccharide synthesis is crucial for understanding biological processes.
  • Traditional methods often require multiple steps and protecting groups.
  • Developing efficient and versatile glycosylation strategies remains a key challenge.

Purpose of the Study:

  • To establish a novel one-pot relay glycosylation protocol.
  • To achieve the formation of two glycosidic bonds with a single activator.
  • To demonstrate the method's utility in synthesizing complex oligosaccharides and natural products.

Main Methods:

  • Utilizing an in situ generated cyclic-thiosulfonium ion as a relay activator.
  • Employing a single equivalent of triflic anhydride for activation.
  • Applying the protocol to a diverse range of substrates for oligosaccharide construction.

Main Results:

  • Successfully constructed two glycosidic bonds in a single pot.
  • Demonstrated accommodation of a wide range of substrates for both linear and branched oligosaccharides.
  • Achieved rapid synthesis of the natural products kankanoside F and merremoside D.

Conclusions:

  • The developed one-pot relay glycosylation is an efficient and advantageous method.
  • The protocol simplifies the synthesis of complex oligosaccharides.
  • This strategy offers a valuable tool for accessing biologically relevant glycosides.