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.
Product Use & Characteristics
Properties of Uracil
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Molecular Formula: C₄H₄N₂O₂
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Molecular Weight: 112.09 g/mol
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IUPAC Name: 1H-pyrimidine-2,4-dione
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Structure: Contains a pyrimidine ring with two keto (carbonyl, C=O) groups at positions 2 and 4.
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Base Pairing: Forms two hydrogen bonds with adenine (A) in RNA.
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Difference from Thymine: Lacks the methyl group (-CH₃) at the 5th carbon, which thymine has.
Role in RNA
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Replacement for Thymine: Replaces thymine in RNA molecules.
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Transcription and Translation: Participates in transcription (copying DNA into RNA) and translation (protein synthesis).
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Types of RNA: Found in messenger RNA (mRNA), transfer RNA (tRNA), and ribosomal RNA (rRNA).
Reasons RNA Uses Uracil Instead of Thymine
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Energetic Efficiency: Uracil is simpler to produce as it does not require methylation.
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Cytosine Deamination: Cytosine can deaminate to form uracil. Since RNA is short-lived, errors are less critical than in DNA.
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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
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Uridine Triphosphate (UTP): Present in UTP, which is used in RNA synthesis.
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Glycolysis: Involved in glycolysis as UDP-glucose.
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Coenzymes: Used in some flavin-containing coenzymes.
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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
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Methyl Group: Thymine has a methyl group at the 5-position, which uracil lacks.
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DNA Repair: DNA repair mechanisms can distinguish and repair deaminated cytosines by removing uracil, which is not normally present in DNA.
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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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