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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.
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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...
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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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Carbohydrates are an essential part of the diet in humans and animals. Grains, fruits, and vegetables are natural sources of carbohydrates that provide energy to the body, particularly through glucose, a simple sugar that is a component of starch and an ingredient in many staple foods. The stoichiometric formula (CH2O)n, where n is the number of carbons in the molecule represents carbohydrates. In other words, the ratio of carbon to hydrogen to oxygen is 1:2:1 in carbohydrate molecules. This...
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Glycosaminoglycans (GAGs), also known as mucopolysaccharides, are long and linear polymers comprising of specific repeating disaccharides - the amino sugar that can be N-acetylglucosamine or N-acetylgalactosamine, and a uronic acid that is usually glucuronic acid or iduronic acid.
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Backbone-modified amphiphilic cyclic di- and tetrasaccharides.

Gour Chand Daskhan1, Narayanaswamy Jayaraman

  • 1Indian Institute of Science, Bangalore 560012, India. jayaraman@orgchem.iisc.ernet.in.

Chemical Communications (Cambridge, England)
|June 24, 2014
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Summary

Researchers synthesized novel amphiphilic cyclic di- and tetrasaccharides with a unique methylene linkage. These compounds show potential as host molecules, demonstrating tunable solubility and stable glycosidic bonds for various applications.

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Area of Science:

  • Carbohydrate Chemistry
  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Cyclic carbohydrates are important scaffolds in supramolecular chemistry.
  • Developing novel carbohydrate-based host molecules with tunable properties is an ongoing area of research.

Purpose of the Study:

  • To synthesize novel amphiphilic cyclic di- and tetrasaccharides incorporating a methylene moiety.
  • To investigate the host-guest properties of the synthesized cyclic tetrasaccharide.
  • To evaluate the stability of the glycosidic bond in the cyclic tetrasaccharide.

Main Methods:

  • Organic synthesis of cyclic di- and tetrasaccharides with a methylene linkage.
  • Solubility studies of guest molecules in aqueous and organic solvents to assess amphiphilic properties.
  • Acid hydrolysis studies to determine glycosidic bond stability.

Main Results:

  • Successful synthesis of amphiphilic cyclic di- and tetrasaccharides.
  • Demonstrated amphiphilic host properties of the cyclic tetrasaccharide through guest solubility assessments.
  • Verified the stability of the glycosidic bond in the cyclic tetrasaccharide under acidic conditions.

Conclusions:

  • The synthesized amphiphilic cyclic tetrasaccharides, particularly the tetrasaccharide, exhibit promising host-guest capabilities.
  • The methylene linkage contributes to the unique amphiphilic nature and stability of these carbohydrate hosts.
  • These novel compounds offer potential for applications in molecular recognition and delivery systems.