Guanine CAS No. 73-40-5

Product Description

Guanine is a fundamental nucleobase found in DNA and RNA, essential for genetic information storage and transmission. As a purine derivative, it features a fused pyrimidine-imidazole ring system with an amino group at the 2-position and a carbonyl group at the 6-position, giving it a planar structure. Guanine pairs with cytosine via three hydrogen bonds, crucial for DNA and RNA stability. It appears as a white crystalline powder, poorly soluble in water and most solvents but soluble in dilute acids and bases. Biologically, guanine is a precursor for guanosine triphosphate (GTP), an energy carrier, and is involved in cellular signaling through cGMP. It is biosynthesized from inosine monophosphate (IMP) and can be derived from guanosine via hydrolysis. Guanine-rich sequences can form G-quadruplexes, influencing gene expression regulation. In non-biological contexts, crystalline guanine is used in cosmetics for its iridescent effect and in simulated pearls and plastics. In nature, it contributes to camouflage and vision in certain animals.

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Product Use & Characteristics

• Chemical Structure:

  • Guanine is a purine derivative with a fused double-ring structure composed of a pyrimidine ring and an imidazole ring.

  • It contains an amino group (-NH₂) at the 2-position and a carbonyl group (C=O) at the 6-position.

  • The molecule is planar due to the conjugated double bonds in the fused pyrimidine-imidazole ring system.

  • Guanine exists in different tautomeric forms, primarily a more stable keto form and a rare enol form, with the keto form being predominant in DNA and RNA.

• Physical Properties:

  • Molecular Formula: C₅H₅N₅O

  • Molar Mass: 151.13 g/mol

  • Appearance: White crystalline powder

  • Solubility: Poorly soluble in water, ethanol, and most organic solvents; soluble in dilute acids and bases due to its weakly amphoteric nature.

  • Melting Point: Around 360°C with partial decomposition due to strong intermolecular hydrogen bonding.

  • Hydrogen Bonding: Forms three hydrogen bonds with cytosine in DNA and RNA, with the C-6 carbonyl group acting as a hydrogen bond acceptor and N-1 and the amino group at C-2 acting as hydrogen bond donors.

• Biological Role:

  • Genetic Information Storage: Guanine is a critical component of DNA and RNA, playing a central role in storing and transmitting genetic information through its specific base pairing with cytosine.

  • Energy Metabolism: Guanine is a component of essential biomolecules involved in energy metabolism, such as guanosine triphosphate (GTP) and cyclic guanosine monophosphate (cGMP). GTP is a vital energy source for processes like protein synthesis and signal transduction.

  • Gene Expression Regulation: Guanine-rich sequences in DNA can form unique secondary structures called G-quadruplexes, which influence the binding of transcription factors and other regulatory proteins, thereby modulating gene expression.

  • Metabolite and Biomarker: Guanine is a metabolite in humans, algae, yeast, E. coli, and mice. Alterations in guanine, such as the presence of 8-oxoguanine (oxidized guanine), can serve as biomarkers for diseases like cancer and genetic disorders, indicating oxidative stress and DNA damage.

Synthesis Methods

• Biosynthesis: Guanine is biosynthesized from inosine monophosphate (IMP) in the purine pathway.

• Derivation: It can be derived from guanosine via hydrolysis.

Uses

• Biological Uses:

  • Molecular Biology and Biochemical Research: Guanine is used in various studies related to DNA and RNA structure, function, and interactions.

  • Drug Development: Guanine is studied in the development of antiviral and anticancer agents due to its role in nucleic acid structure and function.

• Non-Biological Uses:

  • Cosmetics: Crystalline guanine, often obtained from fish scales, is used in the cosmetics industry to provide a pearly, iridescent, or shimmering luster to products like shampoos, eye shadows, nail polishes, and metallic paints. It can also be used as an opacifying agent in skin makeup.

  • Simulated Materials: Guanine is used in simulated pearls and plastics to give them a similar pearly effect.

  • Nature's Camouflage and Vision: In nature, guanine plays a role in camouflage, display, and vision. For example, some animals like spiders and scorpions excrete ammonia as guanine to minimize water loss. It is also found in specialized skin cells of fish (iridocytes) and the eye deposits of deep-sea fish, contributing to vision and camouflaging.

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