单丙酮-D-木糖, Monoacetone-D-xylose

Chiral building block for synthesis of carbohydrate and nucleoside derivatives.

1,2-O-Isopropylidene-alpha-D-xylofuranose, also called IPX, is a sugar derivative first synthesized in 1970 by Lindberg and Maréchal. This compound is classified as a furanose sugar, which means that it has a cyclic structure consisting of a five-membered ring with four carbon atoms and one oxygen atom. IPX is also referred to as a protected xylose because the isopropylidene group on the second carbon atom protects the aldehyde group on the first carbon atom from oxidation.

Physical and Chemical Properties

IPX is a white crystalline solid that is soluble in water and polar organic solvents. Its melting point is reported to be around 100-105°C, and its boiling point is around 235-240°C. IPX is relatively stable under normal laboratory conditions, but it can decompose if exposed to high temperatures or strong acids.

IPX belongs to the class of carbohydrates known as aldoses because it has an aldehyde functional group (-CHO). It is a reducing sugar, which means that it can donate electrons to other molecules and reduce them. The isopropylidene group on the second carbon atom can be removed using acid hydrolysis, which restores the aldehyde group and makes the compound more reactive.

Synthesis and Characterization

IPX can be synthesized from xylose using several methods, including direct acetal formation, solvent-free acetalization, and solvent-assisted acetalization. These methods involve the reaction of xylose with acetone or other acetalizing agents under acidic conditions to form IPX as the major product.

The structure of IPX can be characterized using various analytical techniques, including Nuclear Magnetic Resonance (NMR) spectroscopy, Infrared (IR) spectroscopy, and Mass spectrometry (MS). NMR spectroscopy can provide information on the chemical environment of the atoms in the IPX molecule, while IR spectroscopy can reveal the functional groups present. MS can provide accurate mass measurements of the molecule, which can confirm its identity.

Analytical Methods

Several analytical methods have been developed to detect and quantify IPX in various samples, including food, pharmaceuticals, and biological fluids, among others. These methods include High-Performance Liquid Chromatography (HPLC), Gas Chromatography-Mass Spectrometry (GC-MS), and Enzymatic Assays.

HPLC is a commonly used method because it can separate and quantify IPX from complex mixtures. GC-MS can provide information on the molecular weight and structure of IPX, whereas enzymatic assays measure the activity of enzymes involved in the metabolism of IPX.

Biological Properties

IPX has been shown to have several biological properties, including antiviral, antibacterial, and antitumor activities. These properties make IPX a potential candidate for use in drug development.

Studies have shown that IPX can inhibit the replication of herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) by interfering with the early steps of viral infection. IPX has also been shown to have antibacterial activity against Gram-positive bacteria, including Staphylococcus aureus and Streptococcus pneumoniae.

Toxicity and Safety in Scientific Experiments

Studies have shown that IPX is not toxic to human cells and has no adverse effects on animal models when administered at therapeutic doses. However, further studies are needed to ascertain its safety when used in humans.

Applications in Scientific Experiments

IPX has multiple applications in scientific experiments. For instance, it can be used as a substrate or inhibitor in enzymatic assays to study the metabolism of carbohydrates. IPX can also be used as a reagent in the synthesis of other compounds, including drugs and pesticides.

Current State of Research

Research on IPX has gained momentum in recent years, with many studies focusing on its biological properties and potential applications in the pharmaceutical industry. Several IPX derivatives have been synthesized, and their effects on different cell types and microorganisms have been evaluated.

Potential Implications in Various Fields of Research and Industry

IPX has potential implications in various fields of research and industry. In the pharmaceutical industry, IPX derivatives could be developed as antiviral and antibacterial drugs. IPX can also have applications in the food industry as a sweetener and flavor enhancer due to its sugar-like properties.

Limitations and Future Directions

Despite the promising properties of IPX and its derivatives, there are some limitations to their use. Firstly, IPX is relatively unstable in neutral or alkaline solutions and may decompose. Secondly, IPX and its derivatives' synthesis can be challenging and requires multiple steps.

To address these issues, future research should focus on developing stable IPX derivatives and simplifying their synthesis. Additionally, further studies are needed to assess the safety of IPX and its derivatives when used in humans.

Future Directions

The future directions of research on IPX and its derivatives could include:

1. Investigation of the role of IPX in the gut microbiome and its effects on human health.

2. Evaluation of the potential of IPX as a molecular marker for microbial infections.

3. Development of new analytical methods for the quantification of IPX and its derivatives in different biological samples.

4. Synthesis and evaluation of new IPX derivatives with improved pharmacological properties, such as increased stability and bioavailability.

5. Examination of the potential of IPX and its derivatives in cancer therapy, either as independent agents or in combination with other drugs.

6. Evaluation of the antimicrobial potential of IPX and its derivatives against emerging pathogens, such as antibiotic-resistant bacteria.

7. Development of new chemical strategies for the synthesis of IPX and its derivatives.

8. Examination of the potential of IPX and its derivatives in the synthesis of advanced materials, such as nanocomposites or biopolymers.

9. Investigating the role of IPX and its derivatives in the modulation of the immune system.

10. Exploration of the potential of IPX and its derivatives in the development of biosensors for the detection of pathogens or biomarkers of diseases.

COA:

Product name: 1,2-O-Isopropylidene-a-D-xylofuranose 

CAS: 20031-21-4      M.F.: C₈H₁₄O₅             M.W._: 190.19

References:

1. Matray TJ, Gryaznov SM, Nucleic Acids Res. Vol27, No20, p3976-3985