1. nd naturaNature.263,(5575), 350–1.

2. ^ Jump up to:a b c Kochetkov, N.K. and Budovskii, E.I. Organic Chemistry of Nucleic Acids Part B.
New York: Plenum Press, 1972.
3. ^ Jump up to:a b c Brown, E.G. Ring Nitrogen and Key Biomolecules: The Biochemistry of N-
Heterocycles. Boston: Lluwer Academic Publishers, 1998.
4. Jump up^ Olson, K.C; et al.'Chem Res Toxicol. 24(9), 2011, 1549–1559.

lly occurring pyrimidine derivative.[2] The name "uracil" was coined in 1885 by the German
chemist Robert Behrend, w es[edit]
In RNA, uracil base-pairs with adenine and replaces thymine during DNA
transcription. Methylation of uracil produces thymine.[10] In DNA, the evolutionary substitution of
thymine for uraci red giants or in interstellar dust and gas clouds, according to the scientists.[15]
There are many laboratory syntheses of uracil available. The first reaction is the simplest of the
syntheses, by adding water to cytosine to produce uracil and ammonia:[2]
C4H5N3O + H2O → C4H4N2O2 + NH3
The most common way to synthesize uracil is by the condensation of malic acid with urea
in fuming sulfuric acid:[5]
C4H4O4 + NH2CONH2 → C4H4N2O2 + 2 H2O + CO
Uracil can also be synthesized by a double decomposition of thiouracil in
aqueous chloroacetic acid.[5]
Photodehydrogenation of 5,6-diuracil, which is synthesized by beta-alanine reacting
with urea, produces uracil.[16]

Reactions[edit]
Uracil readily undergoes regular reactions including oxidation, nitration, a
l may have increased DNA stability and improved the efficiency of DNA replication (discussed
below). Uracil pairs with adenine through hydrogen bonding. When base pairingwith adenine,
uracil acts as both a hydrogen bond acceptor and a hydrogen bond donor. In RNA, uracil binds
with a ribose s

e 606623

 CHEBI:17568
ChEBI

ChEMBL  ChEMBL566

ChemSpider  1141

DrugBank  DB03419

ECHA InfoCard 100.000.565

EC Number 200-621-9

Gmelin Reference 2896

IUPHAR/BPS  4560

KEGG  C00106
 PubChem CID  1174

RTECS number YQ8650000

ugar to form the ribonucleoside uridine. When a phosphate attaches to uridine, uridine 5'-
monophosphate is produced.[6]
Uracil undergoes amide-imidic acid tautomeric shifts because any nuclear instability the molecule
ma
ho was attempting to synthesize derivatives of uric acid.[3] Originally discovered in 1900 by
Alberto Ascoli, it was isolated by hydrolysis of yeastnuclein;[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]
Based on 12C/13C isotopic ratios of organic co