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Views: 220 Author: tcchems Publish Time: 2025-08-28 Origin: Site
Content Menu
● Chemical Composition and Molecular Formula
>> Carboxyl Group and Its Importance
>> Hydroxyl Groups and Their Arrangement
● Stereochemistry of Beta-D-Glucopyranosiduronic Acid
>> Beta Anomeric Configuration
>> Importance of Stereochemistry in Biological Function
>> Mutarotation and Ring Interconversion
● Functional Groups and Their Chemical Properties
● Physical Properties and Solution Behavior
>> Ionization and pH Dependence
● Biological Significance and Structural Role
>> Component of Glycosaminoglycans
>> Interaction with Proteins and Enzymes
● Structural Variations and Derivatives
>> Methylation and Esterification
>> Epimers
Beta-D-Glucopyranosiduronic acid is a crucial organic compound with significant biological and chemical importance, widely studied for its role in various biochemical pathways and structural polysaccharides. Understanding the molecular architecture and key properties of this molecule provides valuable insights into its functions and applications in fields such as biochemistry, pharmacology, and materials science. This article delves into the detailed structural features of Beta-D-Glucopyranosiduronic acid, exploring its chemical composition, stereochemistry, ring conformation, and its behavior in aqueous environments.
Beta-D-Glucopyranosiduronic acid is a sugar acid derived from glucose, where the terminal hydroxymethyl group is oxidized to a carboxylic acid. Its molecular formula is C6H10O7, indicating six carbon atoms, ten hydrogen atoms, and seven oxygen atoms.
The defining structural feature is the presence of a carboxyl group (-COOH) at the sixth carbon position, replacing the CH2OH group found in D-glucose. This functional group confers acidic properties to the molecule, capable of dissociating hydrogen ions in aqueous solutions, affecting its solubility and reactivity.
The molecule retains five hydroxyl (-OH) groups on the remaining carbons, critical for hydrogen bonding and interaction with other molecules. The spatial arrangement of these hydroxyl groups defines much of the compound's chemical reactivity and biological recognition.
The stereochemical configuration of Beta-D-Glucopyranosiduronic acid is essential for its biochemical properties and interaction with enzymes and other biomolecules.
The “Beta” in the name indicates the stereochemistry at the anomeric carbon (carbon 1). In the beta configuration, the hydroxyl group at this position is on the same side of the ring as the substituent at the fifth carbon, commonly interpreted as an equatorial orientation in the pyranose ring.
Being a derivative of D-glucose, the stereochemistry at carbon atoms 2, 3, and 4 is retained from the parent sugar molecule, which influences how the molecule fits into enzyme active sites and polysaccharide linkages.
The specific three-dimensional configuration determines how Beta-D-Glucopyranosiduronic acid interacts with enzymes such as glucuronyl transferases and lyases, impacting processes like detoxification in the liver and the formation of structural components in plant cell walls.
Beta-D-Glucopyranosiduronic acid primarily adopts a pyranose ring form, a six-membered ring consisting of five carbon atoms and one oxygen atom.
The most stable conformation is the chair form, where atoms are arranged to minimize steric hindrance and electronic repulsions. In this conformation, substituents occupy either equatorial or axial positions, affecting overall molecular stability.
The oxygen atom within the pyranose ring is integral to the ring closure, bridging the anomeric carbon and carbon 5. This oxygen contributes to the ring's electronic structure and influences the chemical reactivity.
In solution, Beta-D-Glucopyranosiduronic acid can exist in equilibrium between cyclic and open-chain forms, as well as between alpha and beta anomers. Mutarotation is the process by which the compound interconverts between these forms, impacting its optical activity and reactions in aqueous media.
The carboxyl group's acidic nature imparts a pKa value typically around 3–4, meaning that at physiological pH, this group exists mostly in its deprotonated carboxylate form (-COO^-). This negative charge plays an essential role in metal ion binding and interaction with proteins.
Hydroxyl groups are polar and engage in hydrogen bonding, which facilitates water solubility and contributes to intermolecular interactions, such as with enzymes and other biomolecules. Their spatial arrangement also affects glycosidic bond formation.
The carbon at position 1 is unique because it is a hemiacetal center. This site is reactive and responsible for forming glycosidic linkages in polysaccharides, affecting the molecule's participation in larger carbohydrate structures like glycosaminoglycans.
Beta-D-Glucopyranosiduronic acid is highly soluble in water due to its multiple hydroxyl groups and the acidic carboxylate, enabling extensive hydrogen bonding with surrounding water molecules.
The molecule exhibits pH-dependent ionization behavior; the carboxyl group loses a proton to become negatively charged at neutral to alkaline pH, impacting its solubility and interaction with positively charged molecules or ions.
The structural features are often characterized by spectroscopic methods such as Nuclear Magnetic Resonance (NMR) and Infrared (IR) spectroscopy, which identify unique resonances and absorptions correlating to the carboxyl and hydroxyl groups.
Beta-D-Glucopyranosiduronic acid plays a foundational role in biochemistry and physiology due to its presence in important biomolecules.
It constitutes building blocks in glycosaminoglycans like hyaluronic acid, chondroitin sulfate, and heparin. These polysaccharides are vital for extracellular matrices, providing structural support and mediating cell signaling.
The compound is involved in glucuronidation, a process where the glucuronic acid unit conjugates with lipophilic molecules to increase their water solubility and facilitate excretion, especially in the liver.
The specific configuration and functional groups enable selective recognition and binding with enzymes such as glucuronosyltransferases, influencing the metabolism and function of numerous biomolecules.
Several chemical modifications of Beta-D-Glucopyranosiduronic acid expand its structural diversity and functional applications.
Modifications such as methylation of hydroxyl groups or esterification of the carboxyl group alter solubility, binding characteristics, and stability of the molecule, with implications in drug design and biomaterials.
As a monomeric unit, Beta-D-Glucopyranosiduronic acid polymerizes to form polysaccharides with varying chain lengths and sulfation patterns, influencing their biological activities and mechanical properties.
Structural isomers differing in stereochemistry at specific carbon centers can lead to different physical and chemical properties, affecting the biological roles of the resulting compounds.
Beta-D-Glucopyranosiduronic acid exhibits a complex and precise molecular architecture that underpins its diverse biological and chemical functions. Its defining features include the six-membered pyranose ring, the beta anomeric configuration, a carboxyl group at the C6 position, and multiple hydroxyl groups arranged in specific stereochemical orientations. These structural characteristics enable its role in polysaccharide synthesis, detoxification pathways, and molecular recognition processes in living organisms.
1. What distinguishes Beta-D-Glucopyranosiduronic acid from D-glucose?
Beta-D-Glucopyranosiduronic acid differs from D-glucose primarily due to the oxidation of the C6 hydroxymethyl group to a carboxyl group, which gives it acidic properties.
2. Why is the beta configuration important in Beta-D-Glucopyranosiduronic acid?
The beta configuration at the anomeric carbon affects how the molecule interacts with enzymes and forms glycosidic linkages, influencing its biological roles.
3. How does the carboxyl group affect the molecule's behavior in biological systems?
The carboxyl group can ionize, carrying a negative charge at physiological pH, allowing interaction with metal ions and proteins, and aiding solubility in aqueous solutions.
4. What role does Beta-D-Glucopyranosiduronic acid play in the formation of glycosaminoglycans?
It serves as a repeating acidic sugar unit in many glycosaminoglycans, contributing to their negative charge and structural properties in the extracellular matrix.
5. Can Beta-D-Glucopyranosiduronic acid exist in other ring forms?
Yes, though it predominantly exists as a pyranose (six-membered) ring, it can interconvert with open-chain and other cyclic forms in solution through mutarotation.
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