Uracil

Category: Pyrimidine CAS No. 66-22-8

Product Description

Uracil is a pyrimidine nucleobase and one of the four nucleobases in RNA. It has a pyrimidine ring structure with two keto groups at positions 2 and 4. In RNA, uracil pairs with adenine (A) through two hydrogen bonds, playing a crucial role in transcription and translation processes. Unlike thymine in DNA, uracil lacks a methyl group at the 5th carbon, making it simpler to produce and suitable for RNA's short-lived nature. Uracil is found in various RNA types, including mRNA, tRNA, and rRNA. It is also involved in metabolic processes, such as being a component of uridine triphosphate (UTP) used in RNA synthesis and glycolysis. The absence of a methyl group in uracil helps DNA repair systems distinguish and remove uracil from DNA, maintaining genetic stability.

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Product Use & Characteristics

Properties of Uracil

  • Molecular Formula: C₄H₄N₂O₂

  • Molecular Weight: 112.09 g/mol

  • IUPAC Name: 1H-pyrimidine-2,4-dione

  • Structure: Contains a pyrimidine ring with two keto (carbonyl, C=O) groups at positions 2 and 4.

  • Base Pairing: Forms two hydrogen bonds with adenine (A) in RNA.

  • Difference from Thymine: Lacks the methyl group (-CH₃) at the 5th carbon, which thymine has.

Role in RNA

  • Replacement for Thymine: Replaces thymine in RNA molecules.

  • Transcription and Translation: Participates in transcription (copying DNA into RNA) and translation (protein synthesis).

  • Types of RNA: Found in messenger RNA (mRNA), transfer RNA (tRNA), and ribosomal RNA (rRNA).

Reasons RNA Uses Uracil Instead of Thymine

  • Energetic Efficiency: Uracil is simpler to produce as it does not require methylation.

  • Cytosine Deamination: Cytosine can deaminate to form uracil. Since RNA is short-lived, errors are less critical than in DNA.

  • DNA Repair Systems: DNA repair mechanisms can detect and remove uracil in DNA, indicating damage. RNA is continuously synthesized and degraded, so uracil errors are less problematic.

Other Biological Roles

  • Uridine Triphosphate (UTP): Present in UTP, which is used in RNA synthesis.

  • Glycolysis: Involved in glycolysis as UDP-glucose.

  • Coenzymes: Used in some flavin-containing coenzymes.

  • Metabolic Roles: Uridine and its phosphorylated derivatives (UMP, UDP, UTP) act as coenzymes and allosteric regulators in carbohydrate metabolism and polysaccharide biosynthesis.

Comparison with Thymine

  • Methyl Group: Thymine has a methyl group at the 5-position, which uracil lacks.

  • DNA Repair: DNA repair mechanisms can distinguish and repair deaminated cytosines by removing uracil, which is not normally present in DNA.

  • Stability: The methyl group in thymine contributes to the greater stability of DNA compared to RNA, making DNA a more robust long-term storage molecule for genetic information.

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