2-脱氧-D-核糖,  2-Deoxy-D-ribose

2-deoxy-D-Ribose is a reducing sugar formed as a degradation product during metabolism of thymidine by thymidine phosphorylase. It increases levels of reactive oxygen species (ROS) in HL-60 human leukemia cells when used at a concentration of 15 mM. 2-deoxy-D-Ribose (10 µM) induces tubulogenesis and migration of bovine aortic endothelial (BAE) cells. Topical administration of 2-deoxy-D-ribose increases blood vessel formation and accelerates wound healing in a rat full-thickness cutaneous wound model.

Deoxyribose, also known as 2'-deoxy-D-ribose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Deoxyribose exists as a solid, very soluble (in water), and a very weakly acidic compound (based on its pKa). Deoxyribose has been primarily detected in feces.

Used in synthetic organic chemistry and natural product synthesis. Induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione. It is used for synthesis of optically active dipyrrolyl alkanols from pyrroles on the surface of montmorillonite KSF clay.

Deoxyribose is a sugar molecule that is a key component of DNA (Deoxyribonucleic acid), the genetic material of all living organisms. This molecule has been the subject of extensive scientific research since its discovery in the early 20th century and has been found to have a wide range of important properties and functions. The aim of this paper is to provide a comprehensive overview of the various aspects of deoxyribose, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations and future directions.

Definition and Background

Deoxyribose is a pentose sugar that is composed of five carbon atoms, ten hydrogen atoms and four oxygen atoms, and has the chemical formula C5H10O4. It was first isolated in 1929 by Phoebus Levene, who was studying the structure of nucleic acids. At that time, it was believed that the sugar component of nucleic acids was ribose, not deoxyribose. However, further research revealed that DNA contains deoxyribose, whereas RNA (Ribonucleic acid) contains ribose.

Physical and Chemical Properties

Deoxyribose is a white crystalline solid that is soluble in water and has a melting point of 90-93°C. It is a reducing sugar, which means that it can react with other compounds to form glycosides. It also reacts with various amino acids and other organic compounds to form what are known as glycation products. These reactions play important roles in a number of biological processes, including aging and the development of certain diseases.

Synthesis and Characterization

Deoxyribose can be synthesized via a number of different methods, including chemical synthesis and extraction from natural sources such as DNA. The most common method involves the oxidation of ribose using reagents such as hydrogen peroxide or nitric acid. Following this oxidation, the resulting compound is reduced to form deoxyribose. Deoxyribose can be characterized using a range of analytical methods such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy.

Analytical Methods

As noted above, there are a number of analytical methods that can be used to characterize deoxyribose, including HPLC and NMR spectroscopy. These methods allow scientists to study the physical and chemical properties of deoxyribose, determine its purity, and measure the levels of deoxyribose present in different samples.

Biological Properties

Deoxyribose plays a critical role in the biological processes that underpin the functioning of all living organisms. It is a key component of DNA which carries genetic information that determines the traits of an organism. DNA is replicated during cell division and passed on to the next generation. Deoxyribose is also involved in the transcription of DNA into RNA, which in turn codes for the production of proteins.

Toxicity and Safety in Scientific Experiments

Like all chemicals, deoxyribose can be toxic if not handled properly. However, it is generally considered to be safe for use in scientific experiments as long as appropriate precautions are taken. It is important to follow standard laboratory safety procedures and to wear appropriate protective gear when handling deoxyribose.

Applications in Scientific Experiments

Deoxyribose is widely used in a variety of scientific experiments and applications. Its properties and functions make it useful for a range of purposes, including the synthesis of new compounds, as a reagent in biochemical reactions, as a tool for studying the structure and function of DNA, and in the development of new technologies such as DNA sequencing.

Current State of Research

Deoxyribose continues to be an active area of research in both basic and applied science. Scientists are working to better understand its role in DNA, as well as its interactions with other compounds and potential therapeutic applications.

Potential Implications in Various Fields of Research and Industry

Deoxyribose has a wide range of potential applications in various fields of research and industry. These include the development of new drugs and therapies, the development of new technologies for use in fields such as medicine and biotechnology, and the exploration of new avenues for understanding the basic biological processes that underpin life.

Limitations and Future Directions

Despite the various benefits of deoxyribose, there are still limitations and challenges that need to be addressed. For example, more research is needed to understand the molecular mechanisms that underpin the chemical and biological properties of deoxyribose. Additionally, there is a need for the development of new analytical methods and techniques that can be used to better understand this molecule and its functions. Future research may focus on the development of new applications for deoxyribose in fields such as regenerative medicine and biotechnology.

In conclusion, deoxyribose is a unique and vitally important molecule with a wide range of properties and functions. As our understanding of this molecule and its functions continues to evolve, it is likely that we will see the development of new applications and technologies that will have a significant impact on our lives and the lives of future generations.

Title: D-2-Deoxyribose

CAS Registry Number: 533-67-5

CAS Name: 2-Deoxy-D-erythro-pentose

Additional Names: desoxyribose; D-2-deoxyarabinose; D-2-ribodesose; D-erythro-2-deoxypentose; thyminose

Molecular Formula: C5H10O4

Molecular Weight: 134.13

Percent Composition: C 44.77%, H 7.51%, O 47.71%

Literature References: Isoln from deoxyribonucleic acid by acidic hydrolysis of purine deoxyribonucleosides which have been isolated by ion-exchange resin chromatography: Laland, Overend, Acta Chem. Scand. 8, 192 (1954). Synthesis: Felton, Freudenberg, J. Am. Chem. Soc. 57, 1637 (1935); Deriaz et al., J. Chem. Soc. 1949, 1879, 2836; Hough, Chem. Ind. (London) 1951, 406; Sowden, Biochem. Prep. 5, 75 (1957); I. Ziderman, E. Dimant, J. Org. Chem. 32, 1267 (1967); J. R. Hauske, H. Rapoport, ibid. 44, 2472 (1979); T. Harada, T. Mukaiyama, Chem. Lett. 1981, 1109. Review: Overend, Stacey, in Chargaff-Davidson, Nucleic Acids vol. 1, E. Chargaff, N. J. Davidson, Eds. (Academic Press, New York, 1955) pp 1-80.

Properties: Crystals from isopropanol, mp 91°. Shows mutarotation. Final [a]D22 -56.2° (H2O). Sol in water, pyridine. Slightly sol in alc.

Melting point: mp 91°

Optical Rotation: [a]D22 -56.2° (H2O)

Derivative Type: 1,3,4-Triacetate

Molecular Formula: C11H16O7

Molecular Weight: 260.24

Percent Composition: C 50.77%, H 6.20%, O 43.04%

Properties: Needles from methanol, mp 98°. [a]D23 -171.8° (c = 0.56 in chloroform): Allerton, Overend, J. Chem. Soc. 1951, 1480.

Melting point: mp 98°

Optical Rotation: [a]D23 -171.8° (c = 0.56 in chloroform): Allerton, Overend, J. Chem. Soc. 1951, 1480

Derivative Type: 3,4,5-Triacetate

Properties: Oily liq, bp0.001 105°. [a]D21 +3.4° (c = 4.57 in pyridine): Zinner et al., Ber. 90, 2696 (1957).

Boiling point: bp0.001 105°

Optical Rotation: [a]D21 +3.4° (c = 4.57 in pyridine): Zinner et al., Ber. 90, 2696 (1957)

Derivative Type: 1,3,4-Tribenzoate

Properties: Small white nodules from ethanol, mp 127°. [a]D23 -65° (c = 1.02 in chloroform) (Allerton, Overend). Probably a mixture of the two anomeric 2-deoxy-D-ribopyranose tribenzoates: Pedersen et al., J. Am. Chem. Soc. 82, 3425 (1960).

Melting point: mp 127°

Optical Rotation: [a]D23 -65° (c = 1.02 in chloroform) (Allerton, Overend)

Derivative Type: 3,4,5-Tribenzoate

Properties: Fine needles from ethyl acetate + petr ether, mp 118-119°. [a]D18 -2.8° (c = 1.44 in pyridine) (Zinner).

Melting point: mp 118-119°

Optical Rotation: [a]D18 -2.8° (c = 1.44 in pyridine) (Zinner)

COA:

Name: 2-Deoxy-D-ribose    CAS: 533-67-5       M.F.: C₅H₁₀O₄     

M.W.: 134.13           Batch No: 20130628       Quantity: 490g

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Reference:

1. Dueholm KL, Motawia MS, Pedersen EB, Nielsen C, Lundt I, Arch. Pharm. (Weinheim) 1992, Sep 325(9), 597-601