Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Uracil (/ˈjʊərəsɪl/) (symbol U or Ura) is one of the four nucleobases in the nucleic acid RNA. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine (T). Uracil is a demethylated form of thymine.
Uracil is a common and naturally occurring pyrimidine derivative.[2] The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid.[3] Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein;[4] it was also found in bovine thymus and spleen, herring sperm, and wheat germ.[5] It is a planar, unsaturated compound that has the ability to absorb light.[6]
Uracil that was formed extraterrestrially has been detected in the Murchison meteorite,[7] in a near-Earth asteroid,[8] and possibly on the surface of the moon Titan.[9] It has been synthesized under cold laboratory conditions similar to outer space, from pyrimidine embedded in water ice and exposed to ultraviolet light.[10]
^Myers RL (2007). "Chapter 29: Cytosine Thymine and Uracil". The 100 most important chemical compounds : a reference guide. Westport, Conn.: Greenwood Press. pp. 92–93. ISBN 978-0-313-33758-1.
^Garrett RH, Grisham CM (1997). Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning.
^Behrend R (1885). "Versuche zur Synthese von Körpern der Harnsäurereihe" [Experiments on the synthesis of substances in the uric acid series]. Annalen der Chemie. 229 (1–2): 1–44. doi:10.1002/jlac.18852290102. Dasselbe stellt sich sonach als Methylderivat der Verbindung: welche ich willkürlich mit dem Namen Uracil belege, dar. [The same compound is therefore represented as the methyl derivative of the compound, which I will arbitrarily endow with the name ‘uracil’.]
^Ascoli A (1900). "Über ein neues Spaltungsprodukt des Hefenucleins" [On a new cleavage product of nucleic acid from yeast]. Zeitschrift für Physiologische Chemie. 31 (1–2): 161–164. doi:10.1515/bchm2.1901.31.1-2.161. Archived from the original on 12 May 2018.
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^Cite error: The named reference Murch_base was invoked but never defined (see the help page).
^Cite error: The named reference Oba 2023 was invoked but never defined (see the help page).
^Cite error: The named reference Clark 2012 was invoked but never defined (see the help page).
^Cite error: The named reference Nuevo 2009 was invoked but never defined (see the help page).
guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine (T). Uracil is a demethylated form...
nucleobases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA). It is a pyrimidine derivative, with a heterocyclic aromatic ring...
Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism...
thymine may be derived by methylation of uracil at the 5th carbon. In RNA, thymine is replaced with uracil in most cases. In DNA, thymine (T) binds to...
represents various uracil-DNA glycosylases and related DNA glycosylases (EC), such as uracil-DNA glycosylase, thermophilic uracil-DNA glycosylase, G:T/U...
Five nucleobases—adenine (A), cytosine (C), guanine (G), thymine (T), and uracil (U)—are called primary or canonical. They function as the fundamental units...
Uracil dehydrogenase (EC 1.1.99.19, uracil oxidase) is an enzyme with systematic name uracil:(acceptor) oxidoreductase. This enzyme catalyses the following...
nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U). The pyrimidine ring system has wide occurrence in nature as substituted...
urine. Spontaneous deamination is the hydrolysis reaction of cytosine into uracil, releasing ammonia in the process. This can occur in vitro through the use...
nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine (uracil in RNA). In DNA, guanine is paired with cytosine. The guanine nucleoside...
Uracil phosphoribosyltransferase is an enzyme which creates UMP from uracil and phosphoribosylpyrophosphate. This protein may use the morpheein model...
Uracil glycol is a major oxidation product of cytosine in DNA. It can be readily bypassed by E. coli DNA polymerase I (unlike thymine glycol) and be a...
and DNA are: adenine, cytosine, guanine, thymine, and uracil. Thymine occurs only in DNA and uracil only in RNA. Using amino acids and protein synthesis...
catalyzes the chemical reaction O3-acetyl-L-serine + uracil ⇌ {\displaystyle \rightleftharpoons } 3-(uracil-1-yl)-L-alanine + acetate Thus, the two substrates...
to convey genetic information (using the nitrogenous bases of guanine, uracil, adenine, and cytosine, denoted by the letters G, U, A, and C) that directs...
difficult to recognize, but can be repaired by mismatch-specific glycosylases) Uracil inappropriately incorporated in DNA or formed by deamination of cytosine...
is termed mature mRNA.[citation needed] mRNA uses uracil (U) instead of thymine (T) in DNA. uracil (U) is the complimentary base to adenine (A) during...
Abraham Cantarow and Karl Paschkis found liver tumors absorbed radioactive uracil more readily than did normal liver cells. Charles Heidelberger, who had...
cytosine to uracil in DNA by the enzyme activation-induced cytidine deaminase, or AID. A cytosine:guanine pair is thus directly mutated to a uracil:guanine...
hydrolytic deamination to create uracil sulfonate. Under alkaline conditions, uracil sulfonate desulfonates to generate uracil. This enables methylation detection...
thymine and uracil, thymine binds only with adenine, and cytosine and guanine can bind only with one another. Adenine, thymine, and uracil contain two...
Thomas B (1986). "The structures of tetraaqua(uracil-6-carboxylate)zinc(II) monohydrate (A) and tetraaqua(uracil-6-carboxylato)nickel(II) monohydrate (B)"...
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