2-Deoxy-D-ribose
[CAS# 533-67-5]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: 2-Deoxy-D-ribose
• Synonyms: 2-Deoxy-D-arabinose; 2-Deoxy-D-erythropentose; Thyminose
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.13
• CAS Registry Number: 533-67-5
• EC Number: 208-573-0
• SMILES: C(C=O)[C@@H]([C@@H](CO)O)O

Properties

• Water solubility: soluble
• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 90 °C (Expl.)
• alpha: -57 ° (c=1, H2O, 24hr)
• Index of Refraction: 1.580, Calc.^*
• Boiling Point: 332.1±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 154.6±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319-H335
• Safety Statements: P261-P264+P265-P271-P280-P304+P340-P305+P351+P338-P319-P337+P317-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Deoxy-D-ribose is a naturally occurring monosaccharide that plays a crucial role in various biochemical processes, particularly in the synthesis of nucleic acids. It is a structural component of DNA, where it forms the backbone of the double helix. The compound is a derivative of D-ribose, with the key difference being the absence of a hydroxyl group on the second carbon atom. This small modification has significant implications for its function and application in both biological systems and biotechnology.

The discovery of 2-deoxy-D-ribose dates back to the early 20th century when researchers were studying the structure and function of nucleic acids. In the 1920s and 1930s, scientists like Phoebus Levene and Erwin Chargaff made significant contributions to understanding the structure of DNA, which led to the realization that 2-deoxy-D-ribose is an integral component of the DNA molecule. Its role in the deoxyribonucleic acid (DNA) structure is fundamental, as it forms the backbone of the nucleotide structure, linking with phosphate groups and nitrogenous bases to form the long chains of DNA.

2-Deoxy-D-ribose is vital for DNA replication and transcription. It is involved in the formation of nucleotides, the building blocks of DNA. In the body, 2-deoxy-D-ribose is produced from glucose via the pentose phosphate pathway. Once synthesized, it can be incorporated into the DNA during replication, ensuring the proper storage and transfer of genetic information. The absence of the hydroxyl group at the second carbon in 2-deoxy-D-ribose makes the DNA molecule more stable than RNA, which contains ribose, with a hydroxyl group at the second carbon. This difference is crucial for DNA's function in storing genetic material in cells, as it helps protect the molecule from hydrolysis and degradation.

In addition to its biological role, 2-deoxy-D-ribose has found applications in various industries. It is commonly used in molecular biology research, particularly in the synthesis of DNA for cloning, sequencing, and other genetic studies. 2-Deoxy-D-ribose is also essential in the production of synthetic oligonucleotides, which are short DNA fragments used in a wide range of genetic research and diagnostic applications.

The pharmaceutical industry has also seen the potential of 2-deoxy-D-ribose in drug development. It is being explored for its potential in treating conditions related to cellular energy production, such as chronic fatigue syndrome and fibromyalgia. Research suggests that 2-deoxy-D-ribose may play a role in enhancing ATP production, a molecule that cells use for energy. This could have implications for improving energy levels and cellular function in individuals with these conditions.

In the food and nutraceutical industries, 2-deoxy-D-ribose has been marketed as a supplement to improve exercise performance and muscle recovery. Studies have suggested that it may enhance the production of ATP, which could help increase energy levels during physical activity and aid in recovery after exercise.

In conclusion, 2-deoxy-D-ribose is a crucial component of DNA and plays an essential role in genetic material storage, replication, and transcription. Its discovery has had a profound impact on molecular biology and biochemistry. Beyond its biological functions, 2-deoxy-D-ribose has applications in biotechnology, pharmaceuticals, and nutraceuticals, highlighting its versatility and importance across multiple fields.

References

1979. Amino acid catalyzed condensation of purines and pyrimidines with 2-deoxyribose. Biochemistry, 18(13).
DOI: 10.1021/bi00580a026

2000. The iron chelator pyridoxal isonicotinoyl hydrazone (PIH) and its analogues prevent damage to 2-deoxyribose mediated by ferric iron plus ascorbate. Biochimica et Biophysica Acta (BBA) - General Subjects.
DOI: 10.1016/s0304-4165(00)00115-x

2003. The roads to and from the RNA world. Journal of Theoretical Biology, 222(1).
DOI: 10.1016/s0022-5193(03)00020-1