22900-10-3,2-Deoxy-b-D-ribopyranose,CAS:22900-10-3
C5H10O4 / 134.13
2-Deoxy-beta-D-ribopyranose, commonly known as 2-deoxyribose, is a monosaccharide that is structurally similar to ribose, a sugar found in RNA. 2-deoxyribose is found in DNA, where it replaces the hydroxyl group (-OH) on the second carbon of ribose with a hydrogen atom, resulting in the structure of DNA's backbone. This distinctive modification confers unique chemical properties to DNA that distinguish it from RNA and other nucleic acids. The discovery of 2-deoxyribose was an important milestone in understanding the structure and function of DNA.
Physical and Chemical Properties
2-deoxyribose is a white or off-white powder that is soluble in water and organic solvents such as ethanol and methanol. It is a reducing sugar, meaning that it can donate electrons to other molecules and undergo oxidation reactions. 2-deoxyribose has a molecular formula of C5H10O4 and a molecular weight of 134.13 g/mol. It has a melting point of 130-135°C and is stable under standard conditions of temperature and pressure.
Synthesis and Characterization
2-deoxyribose can be synthesized from various starting materials, including glucose and ribose, through a series of chemical reactions. One common method involves the enzymatic reduction of ribose by the enzyme ribonucleotide reductase, which catalyzes the conversion of ribose to 2-deoxyribose by replacing the hydroxyl group on carbon 2 with a hydrogen atom. Another method involves the chemical reduction of ribose using a reducing agent such as sodium borohydride or lithium aluminum hydride.
The identity and purity of 2-deoxyribose can be confirmed using various analytical methods, including nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry. These methods allow researchers to determine the chemical structure, purity, and identity of 2-deoxyribose samples.
Analytical Methods
Various analytical methods can be used to determine the properties and characteristics of 2-deoxyribose. One commonly used method is nuclear magnetic resonance (NMR) spectroscopy, which allows researchers to determine the chemical structure of compounds at the atomic level. NMR spectroscopy can be used to identify the specific chemical bonds, functional groups, and conformational changes in 2-deoxyribose.
Another common method is high-performance liquid chromatography (HPLC), which separates and purifies compounds based on their solubility and chemical properties. HPLC can be used to isolate and quantify 2-deoxyribose from complex mixtures, as well as to assess its purity and identity.
Mass spectrometry (MS) is another powerful analytical tool that can be used to identify and characterize 2-deoxyribose. MS allows researchers to determine the molecular weight, fragmentation patterns, and other chemical properties of compounds by ionizing them and analyzing their mass-to-charge ratios. MS can be used to confirm the identity and purity of 2-deoxyribose samples, as well as to detect impurities or contaminants that may affect its properties or function.
Biological Properties
2-deoxyribose is essential for the structure and function of DNA, which encodes genetic information in all living organisms. DNA is made up of two complementary strands of nucleotides, each of which contains a sugar (2-deoxyribose), a phosphate group, and a nitrogenous base (adenine, guanine, cytosine, or thymine). The unique structure and chemical properties of 2-deoxyribose enable it to form stable hydrogen bonds with other nucleotides, allowing DNA to maintain its double helix structure and store genetic information.
In addition to its role in DNA, 2-deoxyribose is also involved in other biological processes, such as cell signaling and metabolism. For example, it plays a key role in the synthesis of deoxyribonucleotides, which are the building blocks of DNA. Deoxyribonucleotide synthesis involves the reduction of ribonucleotides to their deoxyribonucleotide counterparts, a process that is catalyzed by ribonucleotide reductase and requires 2-deoxyribose as a precursor.
Toxicity and Safety in Scientific Experiments
2-deoxyribose is generally considered to be safe and nontoxic at normal physiological concentrations. However, high concentrations of 2-deoxyribose or its precursors may have toxic effects on cells and tissues. For example, excessive exposure to 2-deoxyribose can cause oxidative stress and DNA damage, which may contribute to the development of various diseases such as cancer, diabetes, and neurodegenerative disorders.
To ensure the safety and reliability of scientific experiments involving 2-deoxyribose, researchers must follow appropriate safety protocols and guidelines. This may include using appropriate protective equipment, handling and storing 2-deoxyribose samples properly, and following established protocols for experimental procedures.
Applications in Scientific Experiments
2-deoxyribose has numerous applications in scientific research, particularly in the fields of molecular biology, biochemistry, and biotechnology. Some common applications of 2-deoxyribose in scientific experiments include:
- Synthesis of DNA and RNA oligonucleotides for use in genetic engineering and gene silencing experiments
- Study of DNA replication, recombination, and repair mechanisms in cells and organisms
- Screening and identification of potential drug targets for the treatment of various diseases such as cancer, autoimmune disorders, and infectious diseases
- Development of new diagnostic and therapeutic technologies based on DNA/RNA hybridization, such as PCR and microarrays
- Investigation of 2-deoxyribose metabolism and its role in cellular signaling and stress responses
Current State of Research
The study of 2-deoxyribose and its applications in scientific research is a rapidly evolving field with many ongoing studies and discoveries. Recent advances in genetic engineering, genomics, and proteomics have opened up new avenues for research on the properties and functions of 2-deoxyribose in cells and organisms.
One area of current research involves the development of new methods for synthesizing and modifying 2-deoxyribose and its analogues. These methods may enable researchers to create new types of DNA/RNA structures with enhanced properties and novel functions.
Another area of current research involves the study of 2-deoxyribose metabolism and its implications for cellular signaling and stress responses. Recent studies have shown that 2-deoxyribose may play a role in regulating various cellular processes such as autophagy, apoptosis, and immune responses.
Potential Implications in Various Fields of Research and Industry
2-deoxyribose and its derivatives have a wide range of potential implications in various fields of research and industry. Some examples of these implications include:
- Development of new therapeutic agents for the treatment of diseases such as cancer, diabetes, and neurodegenerative disorders
- Development of new diagnostic technologies for the detection and monitoring of diseases and genetic disorders
- Production of new materials with enhanced mechanical, electronic, or optical properties based on DNA/RNA structures
- Development of new biocatalysts and enzymes for use in industrial processes such as the production of biofuels, pharmaceuticals, and chemicals.
Limitations and Future Directions
Despite its numerous applications and potential implications, the use of 2-deoxyribose and its derivatives in scientific research and industry is not without limitations and challenges. For example, the synthesis and modification of 2-deoxyribose can be complex and time-consuming, requiring specialized equipment and expertise.
Moreover, some of the current methods for 2-deoxyribose synthesis and modification may be limited by their low yields, low specificity, or high cost. To overcome these limitations and expand the potential applications of 2-deoxyribose, future research may focus on developing novel methods and technologies for its synthesis and characterization.
Future Directions
Some of the future directions that may be pursued in the study of 2-deoxyribose include:
- Development of new methods for the synthesis and modification of 2-deoxyribose and its analogues, such as ribonucleotides and nucleobases
- Exploration of the potential medical applications of 2-deoxyribose and its derivatives, such as cancer therapy and genetic diseases
- Investigation of the properties and functions of 2-deoxyribose in cellular signaling and stress responses, and their potential implications for the development of new therapeutics
- Study of the structural and mechanical properties of DNA/RNA hybrid materials based on 2-deoxyribose, and their applications in materials science and nanotechnology
- Development of new analytical methods and technologies for characterizing and detecting 2-deoxyribose and its derivatives, such as biosensors and imaging techniques.
CAS Number | 22900-10-3 |
Product Name | 2-Deoxy-beta-D-ribopyranose |
IUPAC Name | (2R,4S,5R)-oxane-2,4,5-triol |
Molecular Formula | C5H10O4 |
Molecular Weight | 134.13 g/mol |
InChI | InChI=1S/C5H10O4/c6-3-1-5(8)9-2-4(3)7/h3-8H,1-2H2/t3-,4+,5+/m0/s1 |
InChI Key | ZVQAVWAHRUNNPG-VPENINKCSA-N |
SMILES | C1C(C(COC1O)O)O |
Canonical SMILES | C1C(C(COC1O)O)O |
Isomeric SMILES | C1[C@@H]([C@@H](CO[C@H]1O)O)O |
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