Uracil: Difference between revisions

Revision as of 20:54, 9 February 2025

A nucleobase found in RNA

Uracil is one of the four nucleobases in the nucleic acid of RNA, represented by the letter U. The others are adenine (A), cytosine (C), and guanine (G). Uracil is a pyrimidine derivative and is structurally similar to thymine, another pyrimidine found in DNA.

Structure and properties

Uracil has the chemical formula C₄H₄N₂O₂. It is a planar, unsaturated compound that contains a pyrimidine ring. Uracil can exist in several tautomeric forms, which are in equilibrium with each other. The most common tautomer is the keto form.

Role in RNA

In RNA, uracil base-pairs with adenine through two hydrogen bonds, forming a stable base pair. This pairing is crucial for the structure and function of RNA molecules, including messenger RNA (mRNA), transfer RNA (tRNA), and ribosomal RNA (rRNA).

Biosynthesis and metabolism

Uracil is synthesized in the body through the de novo synthesis pathway of pyrimidines. It is also a product of the breakdown of cytosine. In the cell, uracil is converted into uridine by the addition of a ribose sugar, which is then phosphorylated to form uridine monophosphate (UMP).

Applications and significance

Uracil and its derivatives have several applications in biochemistry and medicine. They are used in the synthesis of various drugs and are important in the study of genetic code and protein synthesis.

Related pages

References

Berg, Jeremy M.; Tymoczko, John L.; Stryer, Lubert (2002). Biochemistry. 5th ed. New York: W.H. Freeman. ISBN 0-7167-4684-0.
Voet, Donald; Voet, Judith G. (2011). Biochemistry. 4th ed. Hoboken, NJ: Wiley. ISBN 978-0-470-57095-1.

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-'''Uracil''' is one of the four [[nucleobase]]s in the [[nucleic acid]] of [[RNA]] that are represented by the letters A, G, C and U. The others are [[adenine]], [[guanine]], and [[cytosine]]. With the formula C4H4N2O2, uracil is a common and naturally occurring [[pyrimidine]] derivative.
+{{short description|A nucleobase found in RNA}}
+{{Use dmy dates|date=October 2023}}
-== Structure and properties ==
+'''Uracil''' is one of the four nucleobases in the nucleic acid of [[RNA]], represented by the letter U. The others are [[adenine]] (A), [[cytosine]] (C), and [[guanine]] (G). Uracil is a pyrimidine derivative and is structurally similar to [[thymine]], another pyrimidine found in [[DNA]].
-Uracil is a planar, unsaturated compound that has the ability to absorb light. The molecule can exist in several tautomeric forms, including the enol form (hydroxy-pyrimidinone), which is more stable in the solid phase and the keto form (oxy-pyrimidine), which is more stable in the solution phase.
-== Functions ==
+==Structure and properties==
-In RNA, uracil base-pairs with adenine and replaces thymine during DNA transcription. Methylation of uracil produces thymine. It turns into [[thymine]] to protect the DNA and to improve the efficiency of DNA replication. Uracil can also be used for energy storage and transfer, as well as in the biosynthesis of the amino acids [[cysteine]] and [[methionine]].
+[[File:Uracil.svg|thumb|right|Chemical structure of uracil]]
+Uracil has the chemical formula C<sub>4</sub>H<sub>4</sub>N<sub>2</sub>O<sub>2</sub>. It is a planar, unsaturated compound that contains a pyrimidine ring. Uracil can exist in several tautomeric forms, which are in equilibrium with each other. The most common tautomer is the keto form.
-== Synthesis ==
+[[File:Uracil_tautomers.png|thumb|right|Tautomeric forms of uracil]]
-Uracil can be made from [[cytosine]] by spontaneous deamination. It can also be synthesized by a condensation reaction between [[malic acid]] and [[urea]] in the presence of heat.
-== Role in disease ==
+==Role in RNA==
-Abnormalities in the enzymes that metabolize uracil have been associated with several human diseases, including [[cancer]], [[neurodegenerative diseases]], and [[congenital metabolic disorders]].
+In [[RNA]], uracil base-pairs with adenine through two hydrogen bonds, forming a stable base pair. This pairing is crucial for the structure and function of RNA molecules, including [[messenger RNA]] (mRNA), [[transfer RNA]] (tRNA), and [[ribosomal RNA]] (rRNA).
-== See also ==
+==Biosynthesis and metabolism==
-* [[Pyrimidine biosynthesis]]
+Uracil is synthesized in the body through the de novo synthesis pathway of pyrimidines. It is also a product of the breakdown of [[cytosine]]. In the cell, uracil is converted into [[uridine]] by the addition of a ribose sugar, which is then phosphorylated to form [[uridine monophosphate]] (UMP).
-* [[Nucleotide]]
-* [[DNA]]
+[[File:Uridin.svg|thumb|right|Structure of uridine]]
+==Applications and significance==
+Uracil and its derivatives have several applications in biochemistry and medicine. They are used in the synthesis of various drugs and are important in the study of [[genetic code]] and [[protein synthesis]].
+==Related pages==
 * [[RNA]]
+* [[Nucleic acid]]
+* [[Pyrimidine]]
+* [[Thymine]]
+==References==
+* Berg, Jeremy M.; Tymoczko, John L.; Stryer, Lubert (2002). ''Biochemistry''. 5th ed. New York: W.H. Freeman. ISBN 0-7167-4684-0.
+* Voet, Donald; Voet, Judith G. (2011). ''Biochemistry''. 4th ed. Hoboken, NJ: Wiley. ISBN 978-0-470-57095-1.
 [[Category:Nucleobases]]
-[[Category:RNA]]
 [[Category:Pyrimidines]]
-{{Chemistry-stub}}
-{{Medicine-stub}}