Chemical structure of vitamin c
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Chemical Structure of Vitamin C
Introduction to Vitamin C Structure
Vitamin C, also known as l-ascorbic acid, is a vital nutrient for human health, playing a crucial role in various cellular processes. Its chemical structure and properties have been extensively studied to understand its biological functions and potential applications.
Molecular Structure of Vitamin C
Basic Structure and Functional Groups
Vitamin C is a carbohydrate-like compound with a molecular formula of C6H8O6. It is characterized by a lactone ring structure, which is essential for its biological activity. The molecule contains several functional groups, including hydroxyl groups and a double bond within the lactone ring, which are critical for its antioxidant properties 23.
Structural Derivatives and Stability
The chemical structure of vitamin C can be modified to produce various derivatives, which can affect its stability and antioxidant capacity. For instance, the double bond in the lactone ring is crucial for its free radical scavenging activity. Modifications to this structure can lead to a slight decrease in antioxidant capacity, especially in aqueous environments 3. These derivatives are often explored to enhance the practical applications of vitamin C in different fields.
Coordination Chemistry of Vitamin C
Metal Complexes
Vitamin C can form complexes with various metal ions, which can alter its chemical properties and potential applications. Studies have shown that ascorbic acid acts as a bidentate ligand, binding through the carbonyl and C-2 enolic hydroxy groups. These complexes often possess an octahedral structure and exhibit paramagnetic properties 19. The formation of such complexes can be significant in biomedical applications, where the interaction with metal ions can influence the biological activity of vitamin C.
Biomedical Importance
The coordination chemistry of vitamin C is not only of academic interest but also has practical implications in medicine. The ability of vitamin C to form complexes with transition metals and rare earth metals can be leveraged to develop new therapeutic agents with enhanced efficacy and stability 1.
Biosynthesis and Enzymatic Pathways
Enzymatic Conversion
In plants, vitamin C is synthesized through multiple metabolic pathways. One key enzyme involved in this process is L-galactose dehydrogenase, which converts L-galactose into L-galactono-1,4-lactone, a precursor of ascorbic acid. The structure of this enzyme, characterized by a (\u03b2/\u03b1)8 barrel, is closely related to aldehyde-keto reductases and plays a crucial role in the biosynthesis of vitamin C 4.
Structural Insights
The structural characterization of enzymes involved in vitamin C biosynthesis provides valuable insights into their function and regulation. For example, the preference of L-galactose dehydrogenase for NAD+ over NADP+ is determined by specific residue substitutions, which influence the enzyme's activity and, consequently, the accumulation of ascorbic acid 4.
Conclusion
The chemical structure of vitamin C, characterized by its lactone ring and functional groups, is fundamental to its biological activity and antioxidant properties. The ability to form metal complexes and the detailed understanding of its biosynthetic pathways further enhance its potential applications in medicine and nutrition. Ongoing research continues to explore the structural modifications and coordination chemistry of vitamin C to develop new derivatives with improved stability and efficacy.
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Most relevant research papers on this topic
The coordination chemistry of Vitamin C: An overview
Vitamin C coordination chemistry encompasses transition metal complexes, rare earth metal complexes, and mixed ligand complexes, with potential biomedical applications.
Literature Review
Highly CitedComparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory
Optimizing vitamin C's chemical structure can decrease its antioxidant capacity slightly in aqueous solvents, but maintaining the double bond of the lactone ring is essential for its free radical scavenging activity.
Structural Characterization of L-Galactose Dehydrogenase: An Essential Enzyme for Vitamin C Biosynthesis
The crystal structure of L-galactose dehydrogenase from spinach reveals its essential role in vitamin C biosynthesis and contributes to a better understanding of structure-function relationships in enzymes involved in vitamin C synthesis.
Isolation and Identification of Vitamin C
This study identifies and isolates a crystalline compound that prevents scurvy in guinea pigs, suggesting it is identical to the LLhexuronic acid studied by Szent-Gyorgyi.
Highly CitedIsolation and Identification of Vitamin C
Vitamin C, a crystalline compound, can be isolated and identified through crystallization, indicating its similarity to LLhexuronic acid, a scurvy-preventing substance found in oranges and cabbage.
Highly CitedFormation of self-assembled polyelectrolyte complex hydrogel derived from salecan and chitosan for sustained release of Vitamin C.
The novel polyelectrolyte complex hydrogel, derived from salecan and chitosan, effectively protects vitamin C from gastric fluid and sustainably releases it in the intestine, improving its assimilation and health benefits.
Highly CitedTherapeutic Perspective of Vitamin C and Its Derivatives
L-ascorbic acid and its derivatives exhibit diverse and potent biological profiles, offering potential for developing new bioactive chemical entities with antioxidant, anticancer, and antiviral properties.
Highly CitedSynthesis and Characterization of Some Metal Complexes of Vitamin C. Part 21—Ascorbate Complexes of Mn(II), Fe(III) and Co(II)
Ascorbic acid complexes with Mn(II), Fe(III), and Co(II) metal ions show promising potential for pharmaceutical applications due to their paramagnetic and octahedral structures.
Vitamin C
Vitamin C is synthesized from d-glucuronate in vertebrates, with its degradation involving 2,3-diketo-l-arginine, CO2, and l-erythrulose.
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