Guanosine
[CAS# 118-00-3]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: Guanosine
• Synonyms: 2-Amino-9-beta-D-ribofuranosyl-9H-purine-6-(1H)-one hydrate; Guanine riboside Guanine riboside; 9-(beta-D-Ribofuranosyl)guanine; Guanine-9-beta-D-ribofuranoside
• Molecular Formula: C₁₀H₁₃N₅O₅
• Molecular Weight: 283.24
• Protein Sequence: N
• CAS Registry Number: 118-00-3
• EC Number: 204-227-8
• SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(NC2=O)N

Properties

• Solubility: 0.75 g/L (water 25 °C)
• Density: 1.4±0.1 g/cm³-Calc.^*
• Melting point: 240 °C
• alpha: -62 ° (c=3, in 0.1 N NaOH)
• Index of Refraction: 1.641, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H301
• Safety Statements: P264-P270-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

Guanosine is a purine nucleoside composed of the nitrogenous base guanine linked to a ribose sugar. It is a fundamental building block of RNA and plays a key role in various biological processes, including cell signaling and metabolism.

Guanosine was first isolated from nucleic acids in the early 20th century. The discovery of nucleosides like guanosine was crucial to understanding the structure and function of nucleic acids. It paved the way for Watson and Crick to elucidate the double helix structure of DNA in 1953 and the subsequent development of molecular biology.

Guanosine is composed of a guanine base linked to a ribose sugar via a β-N9-glycosidic bond. Its structure enables it to pair with cytosine via three hydrogen bonds, contributing to the stability of the nucleic acid structure. The ribose sugar of guanosine can be phosphorylated to form guanosine monophosphate (GMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP), which are essential in energy transfer and signal transduction processes.

Guanosine is a component of RNA and is involved in the encoding of genetic information and the synthesis of proteins. In RNA, guanosine pairs with cytosine, ensuring accurate transfer of genetic information during transcription and translation.

Guanosine derivatives such as GTP are essential in cellular energy transfer. GTP is a substrate for RNA synthesis during transcription and plays a vital role in protein synthesis as an energy source during translation.

GTP and its derivatives are key players in signal transduction pathways. GTP-binding proteins such as G proteins act as molecular switches in various cellular processes, including signal transduction, cell growth, and differentiation.

Guanosine and its metabolites are involved in cellular metabolism. GTP is essential in gluconeogenesis, the synthesis of glucose from non-carbohydrate sources, and in the function of the citric acid cycle.

Guanosine analogs such as acyclovir and ganciclovir are used as antiviral agents. These compounds mimic guanosine and interfere with viral DNA synthesis, thereby inhibiting the replication of viruses such as herpes simplex and cytomegalovirus.

Guanosine has neuroprotective properties and is currently being investigated for its potential in treating neurodegenerative diseases such as Alzheimer's and Parkinson's diseases. It is thought to regulate glutamate uptake and reduce oxidative stress, thereby exerting neuroprotective effects.

Guanosine analogs are also being studied for their potential in cancer treatment. Some analogs can inhibit DNA synthesis in rapidly dividing cancer cells, leading to cell death. This makes them promising anticancer drug candidates.

In research laboratories, guanosine and its derivatives are used to study RNA synthesis, signal transduction pathways, and enzyme activity. Their role in various biochemical processes makes them valuable tools for understanding cellular mechanisms.

References

2025. Guanosine hydrogels in focus: A comprehensive analysis through mid-infrared spectroscopy. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 324, 124939.
DOI: 10.1016/j.saa.2024.124939

2024. DNA-Free Guanosine-Based Polymer Nanoreactors with Multienzyme Activities for Ferroptosis-Apoptosis Combined Antitumor Therapy. ACS Nano, 18(47), 31936-31950.
DOI: 10.1021/acsnano.4c11275

1998. Process of guanosine production by fermentation. Gongye Weishengwu, 28(4), 11-16.