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Views: 220 Author: tcchems Publish Time: 2025-07-21 Origin: Site
Content Menu
● Understanding Beta-D-Glucopyranosiduronic Acid
>> What is Beta-D-Glucopyranosiduronic Acid?
● Beta-D-Glucopyranosiduronic Acid vs Other Glucuronides
>> Structural and Functional Differences
● Biological Roles and Metabolic Pathways
>> Beta-D-Glucopyranosiduronic Acid in the Body
>> Formation of Glucuronides via Glucuronidation
● Beta-D-Glucopyranosiduronic Acid in Drug Metabolism and Detoxification
>> Detoxifying Role of Glucuronides
>> Examples
● Enzymatic Interactions: Beta-D-Glucuronidase and Glucuronides
● Applications and Research Focuses
>> Structural Diversification of Glucuronides
>> Therapeutic and Diagnostic Uses
● Summary
● Frequently Asked Questions (FAQs)
Glucuronides are a broad class of biochemical conjugates formed mainly through the enzymatic addition of glucuronic acid to various substrates. Among them, Beta-D-glucopyranosiduronic acid holds a distinctive place because of its structural and functional properties. This article provides an in-depth exploration of Beta-D-glucopyranosiduronic acid, contrasting it with other glucuronides to clarify their unique biochemical roles, formation pathways, and implications in metabolism and health.
Beta-D-glucopyranosiduronic acid is a sugar acid derived from glucose where the sixth carbon's primary alcohol group is oxidized to a carboxylic acid, forming D-glucuronic acid in a beta-anomeric pyranose ring form. Its molecular formula is C6H10O7, and it acts as a key metabolite within several biological processes. Notably, the beta configuration at the anomeric carbon differentiates it from alpha forms and influences its biological recognition and enzyme specificity.
This compound serves as a conjugate acid of beta-D-glucuronate and is a monomeric unit in polysaccharides like hyaluronic acid and heparin, essential components of the extracellular matrix and connective tissues.
- The molecule exists predominantly in a six-membered pyranose ring form.
- Contains a carboxyl group at C6 replacing the typical primary hydroxyl group.
- Possesses multiple hydroxyl groups contributing to its polarity and solubility.
Its distinctive beta configuration and carboxyl function facilitate its coupling to a wide variety of endogenous and xenobiotic molecules through glycosidic bonds.
Glucuronides are molecules formed when glucuronic acid attaches to another molecule—usually a xenobiotic (foreign compound), endogenous metabolite, or drug—through glycosidic linkage. This process, termed glucuronidation, enhances the solubility and excretion of hydrophobic substances.
In most animals, including humans, glucuronidation is a critical pathway in phase II metabolism catalyzed by UDP-glucuronosyltransferases (UGTs), which transfer glucuronic acid from UDP-glucuronic acid to substrates.
- Phenolic glucuronides: where glucuronic acid attaches to hydroxyl groups of phenolic compounds (e.g., phenyl beta-D-glucopyranosiduronic acid).
- Alcohol glucuronides: attachment at hydroxyl groups of alcohols.
- Carboxylic acid glucuronides: binding through ester bonds.
- Amine glucuronides: binding to nitrogen atoms of amines.
The diversity of glucuronides depends on both the accepting molecule and the site of conjugation.
| Feature | Beta-D-Glucopyranosiduronic Acid | Other Glucuronides |
|---|---|---|
| Chemical nature | A monosaccharide acid with beta-anomeric pyranose form | Conjugates of glucuronic acid with diverse molecules |
| Function | Building block of larger molecules; also a conjugation donor | Metabolites formed by glucuronidation of exogenous and endogenous substances |
| Molecular weight | ~194 g/mol | Variable depending on conjugated moiety |
| Role in metabolism | Directly a metabolite or monomer (e.g., hyaluronic acid) | Detoxification via increased water solubility |
| Enzymatic formation | Generated in biosynthetic pathways | Formed mainly by UGT enzymes during xenobiotic metabolism |
| Molecular complexity | Simple monosaccharide acid | Complex conjugates, sometimes very large molecules |
- Beta-D-glucopyranosiduronic acid forms the base molecule for all glucuronides; thus, all glucuronides retain its core structure but acquire distinct properties depending on conjugated substrates.
- Other glucuronides vary vastly in size, hydrophobicity, and biological targets, as they reflect the chemical nature of the attached molecules.
- For example, phenyl beta-D-glucopyranosiduronic acid is a glucuronide where phenol is conjugated with beta-D-glucopyranosiduronic acid, modulating its solubility and biological effects.
- Complex glucuronides, including conjugates with drugs, flavonoids, or toxins, serve detoxification and excretion roles, enhancing elimination from the body.
Beta-D-glucopyranosiduronic acid is not only an intermediate metabolite but also a building block in polysaccharides such as hyaluronic acid, a key component of connective tissues, synovial fluid, and skin. It contributes to the structural integrity and hydration properties of tissues.
Glucuronidation involves:
1. Activation: UDP-glucuronic acid is synthesized in the liver.
2. Transfer: UGT enzymes attach glucuronic acid in beta configuration to substrates' functional groups.
3. Excretion: Increased solubility allows excretion via bile or urine.
For example, drugs like ethanol get metabolized into ethyl-β-D-glucuronide, a minor but important metabolite used in forensic analysis.
Glucuronidation of drugs and toxins alters their chemical properties:
- Increases water solubility,
- Facilitates renal or biliary elimination,
- Reduces toxicity.
Beta-D-glucopyranosiduronic acid itself is the moiety that enables these properties in the glucuronide conjugates.
- Flavonoid glucuronides (conjugates with Beta-D-glucopyranosiduronic acid) show altered bioavailability and antioxidant activity.
- Certain phenolic compounds when glucuronidated impact bacterial gut flora due to β-D-glucuronidase activities releasing the phenol and glucuronic acid in the gut, influencing microbiome-host interactions.
Human and microbial beta-D-glucuronidases (GUSs) can hydrolyze glucuronides, releasing free glucuronic acid and the aglycone (non-sugar moiety). This reaction is essential in gut microbial metabolism but may also affect drug efficacy and toxicity.
- Variation in degradation rates of glucuronides by different bacterial species can influence intestinal health.
- Beta-D-glucopyranosiduronic acid derived glucuronides may have different susceptibilities to enzymatic cleavage depending on the substrate conjugated.
Recent studies have synthesized various phenyl β-D-glucuronides with different substituents to understand their enzymatic degradation and impact on bacterial growth.
- Measurement of specific glucuronides like ethyl-β-D-glucuronide helps detect alcohol consumption.
- Investigations into glucuronide metabolism open avenues in understanding drug interactions and microbial influences.
Beta-D-glucopyranosiduronic acid is a fundamental biochemical unit of glucuronides, distinguished by its molecular structure and biological roles. Compared to complex glucuronides formed by coupling with diverse molecules, it serves both as a metabolite and a structural moiety within larger macromolecules. The glucuronidation process, vital for detoxification and metabolic regulation, hinges on Beta-D-glucopyranosiduronic acid's unique chemical properties. The differences between it and other glucuronides underscore the diversity and specificity of glucuronide-mediated pathways in physiology, drug metabolism, and microbiota interactions.
Q1: What is the primary role of Beta-D-glucopyranosiduronic acid in metabolism?
A1: It serves as a building block for important biomolecules like hyaluronic acid and as the glucuronide donor in phase II metabolism for detoxification.
Q2: How does Beta-D-glucopyranosiduronic acid differ structurally from other glucuronides?
A2: It is a simple sugar acid with a beta-pyranose ring, whereas other glucuronides are conjugates formed by attaching this sugar acid to various substrates.
Q3: What enzymes are responsible for forming glucuronides involving Beta-D-glucopyranosiduronic acid?
A3: UDP-glucuronosyltransferases (UGTs) catalyze the transfer of Beta-D-glucopyranosiduronic acid to substrates.
Q4: Can Beta-D-glucopyranosiduronic acid be released back from glucuronides?
A4: Yes, human and microbial beta-D-glucuronidases hydrolyze glucuronides, freeing glucuronic acid.
Q5: Why is glucuronidation important in pharmacology?
A5: It enhances drug solubility and elimination, reducing toxicity and aiding in drug clearance.
[1] https://pubs.acs.org/doi/10.1021/acsomega.4c09036
[2] https://pubchem.ncbi.nlm.nih.gov/compound/441478
[3] https://pubchem.ncbi.nlm.nih.gov/compound/Phenyl-beta-D-glucopyranosiduronic-acid
[4] https://pubchem.ncbi.nlm.nih.gov/compound/122361323
[5] https://pmc.ncbi.nlm.nih.gov/articles/PMC5954986/
[6] http://cn.bing.com/dict/glucuronide?mkt=zh-CN&setlang=ZH
[7] https://www.sciencedirect.com/topics/neuroscience/glucuronide
[8] https://pubchem.ncbi.nlm.nih.gov/compound/6452798
[9] https://www.caymanchem.com/product/22271/ethyl-%CE%B2-d-glucuronide
[10] https://eng.ichacha.net/glucuronic%20acid.html
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