C-glycosidic bond

Definition

A c-glycosidic bond is a type of glycosidic bond where the anomeric carbon of a sugar is connected to a carbon atom of another molecule, forming a stable linkage. This type of bond differs from the more common O-glycosidic bonds, which involve an oxygen atom bridging the two molecules. C-glycosidic bonds are significant in biochemistry as they contribute to the structural diversity and stability of certain compounds like flavonoids and glycosylated natural products.

5 Must Know Facts For Your Next Test

1. C-glycosidic bonds are more stable than O-glycosidic bonds because they do not easily undergo hydrolysis.
2. These bonds are commonly found in bioactive compounds like flavonoids, which play important roles in plant biology and human health.
3. The formation of c-glycosidic bonds typically involves specific enzymes called glycosyltransferases.
4. C-glycosides can exhibit unique biological activities compared to their O-glycoside counterparts due to differences in their stability and reactivity.
5. Research has shown that c-glycosides can have enhanced pharmacological properties, making them attractive candidates for drug development.

Review Questions

• Compare and contrast c-glycosidic bonds with O-glycosidic bonds in terms of their stability and biological significance.
  • C-glycosidic bonds are generally more stable than O-glycosidic bonds, primarily because c-glycosides resist hydrolysis under physiological conditions. This stability allows c-glycosides to have longer-lasting effects in biological systems, making them significant in various plant-derived compounds like flavonoids. While O-glycosidic bonds are prevalent in many carbohydrates, the presence of c-glycosidic bonds contributes to unique properties and functionalities in compounds that may have therapeutic potential.
• Discuss the role of glycosyltransferases in the formation of c-glycosidic bonds and how this process impacts biochemical pathways.
  • Glycosyltransferases are enzymes responsible for facilitating the formation of c-glycosidic bonds by transferring carbohydrate moieties to acceptor molecules. This enzymatic activity plays a crucial role in various biochemical pathways, influencing the biosynthesis of important secondary metabolites such as flavonoids. The regulation of these enzymes can impact the overall metabolic profile of plants and their responses to environmental stimuli or stresses.
• Evaluate the potential implications of c-glycosides in drug development, considering their unique properties compared to O-glycosides.
  • C-glycosides present exciting opportunities for drug development due to their enhanced stability and distinctive biological activities compared to O-glycosides. Their resistance to enzymatic degradation allows for prolonged efficacy in therapeutic applications. Additionally, research indicates that c-glycosides may interact differently with biological targets, potentially leading to novel mechanisms of action. By leveraging these properties, scientists aim to design more effective and sustainable pharmaceuticals that capitalize on the benefits offered by c-glycosides.

Related terms

O-glycosidic bond: A glycosidic bond where an anomeric carbon of a sugar is linked to an oxygen atom in another molecule.

Anomeric carbon: The carbon atom in a carbohydrate that is derived from the carbonyl carbon and is the site of glycosidic bond formation.

Flavonoids:

A class of plant secondary metabolites known for their antioxidant properties and often containing c-glycosidic bonds.