D-Lyxose CAS 1114-34-7

D-Lyxose is a six-carbon monosaccharide belonging to the class of rhamnose. Its chemical formula is C5H10O5, CAS 1114-34-7, and its molecular weight is 150.13. It is white crystalline powder at room temperature, odorless and tasteless. The solubility in water is 16.7 g/100 mL (20°C), the solubility in methanol is 2.9 g/100 mL (20°C), insoluble in ethanol. Typically, the solubility of monosaccharide molecules is closely related to their chemical structure and environmental factors. For example, the oxygen-containing functional groups of it make it more hydrophilic, so it has relatively high solubility in water. It is an asymmetric molecule, so it has optical activity. The specific rotation ([α]) of it is +17.0° (at 20°C, at 590 nm, with water as solvent). It should be pointed out that specific optical rotation is a property with large influence factors, and its value is affected by many factors such as compound configuration, ambient temperature, wavelength, and concentration. It has a variety of application fields, including food, medicine, biotechnology and other aspects. With the continuous deepening of the research on it, its application fields will also continue to expand.

► Chemical Structure

D-Lyxose is a pentose monosaccharide, meaning it consists of five carbon atoms in its backbone. It belongs to the aldopentose family, characterized by the presence of an aldehyde functional group (-CHO) at the first carbon position (C1). The carbon atoms in D-Lyxose are numbered from C1 to C5, with each carbon atom bearing specific functional groups that define its chemical properties.

The configuration of the hydroxyl (-OH) groups attached to the carbon atoms is crucial in determining the stereochemistry of D-Lyxose. In D-Lyxose, the hydroxyl group at C2 is on the right side (in the Fischer projection), the hydroxyl group at C3 is on the left side, and the hydroxyl group at C4 is on the right side. This specific arrangement of hydroxyl groups gives D-Lyxose its unique identity and distinguishes it from other pentose sugars such as D-ribose and D-arabinose.

► Physical Properties

D-Lyxose is a white crystalline solid with a sweet taste, although its sweetness is less intense compared to common sugars like sucrose. It has a melting point of approximately 105 - 107°C and is soluble in water, with a solubility that increases with temperature. The compound exhibits a specific rotation of [α]D²⁰ +18.0° (c = 2 in water), which is a characteristic property used to identify and distinguish it from other sugars.

The chemical reactivity of D-Lyxose is influenced by the presence of its aldehyde group and multiple hydroxyl groups. The aldehyde group can undergo oxidation reactions to form carboxylic acids, while the hydroxyl groups can participate in esterification, etherification, and glycosidic bond formation reactions. These chemical properties make D-Lyxose a versatile compound that can be modified and utilized in various chemical and biological applications.

► Medical Applications

1) Antiviral Agents

Recent studies have suggested that D-Lyxose and its derivatives may have potential antiviral activity. Some researchers have found that certain compounds derived from D-Lyxose can inhibit the replication of viruses such as herpes simplex virus (HSV) and human immunodeficiency virus (HIV). The antiviral mechanism of these compounds is thought to involve the inhibition of viral enzymes or the interference with viral entry into host cells. Further research is needed to fully understand the antiviral potential of D-Lyxose and its derivatives and to develop them into effective antiviral drugs.

2) Anticancer Agents

D-Lyxose and its analogs may also have potential as anticancer agents. Some studies have shown that certain D-Lyxose-containing compounds can induce apoptosis (programmed cell death) in cancer cells and inhibit tumor growth in animal models. The anticancer mechanism of these compounds may involve the modulation of cell signaling pathways, the induction of oxidative stress, or the interference with tumor angiogenesis. However, more research is required to determine the safety and efficacy of D-Lyxose-based anticancer agents in clinical settings.

3) Diagnostic Tools

In the field of medical diagnostics, D-Lyxose can be used as a building block for the synthesis of carbohydrate-based probes and sensors. For example, D-Lyxose can be conjugated to fluorescent dyes or other reporter molecules to create probes that can specifically recognize and bind to certain carbohydrates or glycoconjugates on the surface of cells. These probes can then be used to detect and visualize cells or tissues with specific carbohydrate profiles, which may be useful for the diagnosis of diseases such as cancer, inflammation, and infectious diseases.

► Biotechnological Applications

1) Enzyme Engineering

D-Lyxose can be used as a substrate for enzyme engineering studies. By studying the enzymes that metabolize D-Lyxose, researchers can gain insights into the structure-function relationships of these enzymes and use this knowledge to engineer enzymes with improved catalytic properties. For example, lyxose isomerase, the enzyme that converts D-Lyxose to D-xylulose, can be engineered to increase its activity, stability, or substrate specificity, which may have applications in the bioconversion of D-Lyxose-containing biomass into valuable chemicals and fuels.

2) Biopolymer Synthesis

D-Lyxose can also be used as a monomer for the synthesis of biopolymers. By polymerizing D-Lyxose with other monosaccharides or functional groups, researchers can create novel biopolymers with unique physical and chemical properties. These biopolymers may have applications in areas such as drug delivery, tissue engineering, and environmental remediation. For example, D-Lyxose-based hydrogels can be designed to have controlled swelling properties and biocompatibility, making them suitable for use as drug carriers or scaffolds for tissue regeneration.

3) Nutritional Applications

Although D-Lyxose is not a major dietary sugar, it may have potential nutritional benefits. Some studies have suggested that D-Lyxose can be used as a low-calorie sweetener or a prebiotic. As a low-calorie sweetener, D-Lyxose can provide sweetness without contributing significantly to calorie intake, which may be beneficial for individuals who are trying to manage their weight or control their blood sugar levels. As a prebiotic, D-Lyxose can promote the growth of beneficial gut bacteria, which may improve gut health and enhance the immune system. However, more research is needed to fully evaluate the nutritional properties and safety of D-Lyxose as a food ingredient.

► Industrial Applications

D-Lyxose isomerase (D-LI) has emerged as a biocatalyst for synthesizing high-value sugars, including D-mannose, L-ribose, and D-xylulose. These sugars have applications in:

Food Industry: D-mannose promotes gut health by stimulating the growth of beneficial bacteria like Lactobacillus and Bifidobacterium. It is used in probiotic supplements and functional foods.

Pharmaceuticals: L-ribose serves as a precursor for antiviral and anticancer nucleoside analogs, such as lamivudine and telbivudine. Its synthesis via D-LI-catalyzed isomerization of L-arabinose offers a cost-effective alternative to chemical methods.

Cosmetics: D-xylulose acts as a humectant and antioxidant in skincare products, enhancing moisture retention and protecting against oxidative stress.

Despite the potential applications of D-Lyxose, there are several challenges that need to be addressed. One of the main challenges is the limited availability of D-Lyxose. Since D-Lyxose is relatively rare in nature, its production on a large scale can be costly and time-consuming. Researchers are exploring various methods for the synthesis of D-Lyxose, including chemical synthesis and biotechnological approaches using enzymes or microorganisms. However, these methods still need to be optimized to improve yield and reduce costs.

Another challenge is the lack of understanding of the biological functions and mechanisms of action of D-Lyxose in different organisms. Although some studies have suggested potential roles for D-Lyxose in carbohydrate metabolism, glycobiology, and disease processes, more research is needed to fully elucidate these functions and to identify potential targets for therapeutic intervention.

In the future, research on D-Lyxose is likely to focus on several areas. First, further studies will be conducted to optimize the synthesis and production of D-Lyxose, making it more accessible for various applications. Second, more in-depth research will be carried out to understand the biological functions and mechanisms of action of D-Lyxose in different organisms, which may lead to the discovery of new therapeutic targets and biomarkers. Finally, the potential applications of D-Lyxose in medicine, biotechnology, and nutrition will be further explored and developed, with the goal of translating basic research findings into practical applications that can benefit human health and well-being.

D-Lyxose is a versatile pentose sugar with significant potential in biotechnology, pharmaceuticals, and food science. Its unique stereochemistry, metabolic relevance, and enzymatic convertibility make it a valuable target for research and industrial applications. As synthetic biology and biocatalysis technologies continue to evolve, D-Lyxose is poised to play a pivotal role in the development of sustainable and innovative solutions for global health and nutrition challenges.

By leveraging its multifaceted properties, scientists and industries can unlock new opportunities for D-Lyxose in functional food ingredients, antiviral therapies, and green chemistry-ushering in a new era of biochemical innovation.

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