D-Ribose
[CAS# 50-69-1]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: D-Ribose
• Synonyms: D(-)-Ribose
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• CAS Registry Number: 50-69-1
• EC Number: 200-059-4
• FEMA: 3793
• SMILES: C([C@H]([C@H]([C@H](C=O)O)O)O)O

Properties

• Solubility: 0.1 g/mL (H2O) (Expl.)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 88 – 92 °C (Expl.)
• alpha: -20.8 ° (c=4, H2O)
• Index of Refraction: 1.544, Calc.^*
• Boiling Point: 415.5±38.0 °C (760 mmHg), Calc.^*
• Flash Point: 219.2±23.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

D-Ribose is a naturally occurring monosaccharide, or simple sugar, that plays a crucial role in cellular metabolism. It is classified as a pentose sugar, meaning it contains five carbon atoms, and it is specifically a component of RNA (ribonucleic acid). D-Ribose is also a key component of ATP (adenosine triphosphate), which is essential for energy transfer in cells. The molecular formula of D-Ribose is C5H10O5, and it exists in an aldopentose configuration, meaning it has an aldehyde group attached to one of its carbon atoms.

The discovery of D-Ribose traces back to the early 20th century, during studies on the structure and function of nucleic acids. It was first isolated and characterized as a component of ribonucleic acid by Phoebus Levene in the 1920s. Levene's work on the structure of nucleotides and nucleic acids laid the foundation for our understanding of the role of sugars like D-ribose in cellular processes. The identification of D-ribose as a sugar component of RNA was significant in advancing the understanding of genetic material and cellular biochemistry.

D-Ribose is widely used in biochemistry and molecular biology due to its critical role in several biological processes. One of its primary applications is in the synthesis of nucleotides, which are the building blocks of nucleic acids such as RNA and DNA. D-Ribose serves as the sugar component in RNA, where it forms part of the backbone of the RNA strand, linking with phosphate groups and nitrogenous bases to create the complete structure of RNA. This role in RNA makes D-ribose essential for the processes of transcription and translation, which are key to protein synthesis and cellular function.

Another important application of D-Ribose is its involvement in the formation of ATP, a molecule that stores and transfers energy within cells. ATP consists of adenine (a nitrogenous base), ribose (a sugar), and three phosphate groups. The high-energy bonds between the phosphate groups in ATP are broken to release energy, which is used in various metabolic processes, including muscle contraction, protein synthesis, and cellular signaling. Given that ATP is vital for virtually all cellular activities, the role of D-ribose in ATP synthesis underscores its importance in cellular energy metabolism.

D-Ribose has been studied for its potential therapeutic applications, particularly in conditions involving impaired cellular energy metabolism. One area of interest is its use in the treatment of chronic fatigue syndrome (CFS) and fibromyalgia. Research suggests that D-ribose supplementation may help improve energy production in cells and alleviate fatigue symptoms in patients suffering from these conditions. Some clinical studies have reported that D-ribose supplementation may enhance the energy production in muscles, leading to improved physical performance and reduced fatigue. However, while promising results have been observed, further research is needed to fully establish the effectiveness and safety of D-ribose for these conditions.

In addition to its potential therapeutic uses, D-ribose has applications in the food and pharmaceutical industries. It is sometimes used as a sweetener in certain food products, although its use is less common than other sugars. It is also used in the production of certain medicines, particularly in formulations designed to improve energy production or enhance recovery in conditions related to energy deficits. D-Ribose has been incorporated into dietary supplements marketed to athletes and individuals seeking to boost their energy levels and performance.

D-Ribose is also employed in research and laboratory settings, particularly in the study of nucleic acids, metabolism, and cellular energetics. It is utilized in the synthesis of RNA and other nucleotides for experimental purposes, contributing to advancements in molecular biology, genetics, and drug development.

In conclusion, D-ribose is a biologically significant sugar that plays a central role in nucleic acid structure, cellular energy production, and metabolism. Its discovery and subsequent applications in various scientific and medical fields highlight its importance in both basic biological processes and therapeutic interventions. While research into its clinical benefits continues, D-ribose remains a key molecule in biochemistry and medicine.

References

2007. Selective Bond Breaking in β-D-Ribose by Gas-Phase Electron Attachment around 8 eV. Journal of the American Chemical Society, 129(16).
DOI: 10.1021/ja070542h

2008. D-Ribose Benefits Restless Legs Syndrome. Journal of Alternative and Complementary Medicine, 14(9).
DOI: 10.1089/acm.2008.0227

2010. DNA damage by ribose: inhibition at high ribose concentrations. Indian Journal of Biochemistry & Biophysics, 47(3).
PMID: 20653285