Uracil

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
Uracil
by the German
chemist Robert
Behrend, who was
attempting to
synthesize
derivatives of uric
acid.[3] Originally
Names
discovered in 1900
by Alberto Ascoli, it Preferred IUPAC
was isolated by name
Pyrimidine-
hydrolysis of yeast
2,4(1H,3H)-
nuclein;[4] it was dione
also found in bovine Other names
thymus and spleen, 2-Oxy-4-
herring sperm, and oxypyrimidine
wheat germ.[5] It is a 2,4(1H,3H)-
planar, unsaturated Pyrimidinedione

compound that has 2,4-

Dihydroxypyrimidi
the ability to absorb
ne
light.[6]
2,4-Pyrimidinediol

Uracil that was Identifiers

formed CAS 66-22-8

extraterrestrially has Number
(https://c
been detected in the ommonc
Murchison hemistry.

meteorite,[7] in a cas.org/
detail?ca
near-Earth
s_rn=66-
asteroid,[8] and
22-8)
possibly on the
surface of the moon
Titan.[9] It has been 3D lactam
model
synthesized under form:
(JSmol)
cold laboratory Interactive

conditions similar to image (htt

ps://chem
outer space, from
apps.stola
pyrimidine
f.edu/jmo
embedded in water
l/jmol.ph
ice and exposed to p?model=
ultraviolet light.[10] O%3DC1
C%3DCN
Properties
C%28%3D
In RNA, uracil base- O%29N1)
pairs with adenine lactim

and replaces form:

Interactive
thymine during DNA
image (htt
transcription.
Methylation of uracil ps://chem
produces apps.stola

thymine.[11] In DNA, f.edu/jmo

l/jmol.ph
the evolutionary
p?model=
substitution of
Oc1nccc%
thymine for uracil
28O%29n
may have increased 1)
DNA stability and
3DMet B00026
improved the
(http://w
efficiency of DNA ww.3dm
replication et.dna.af
(discussed below). frc.go.jp/
Uracil pairs with cgi/show

adenine through _data.ph

p?acc=B
hydrogen bonding.
00026)
When base pairing
with adenine, uracil Beilstein 606623
Reference
acts as both a
hydrogen bond ChEBI CHEBI:17568

acceptor and a (https://ww

w.ebi.ac.uk/c
hydrogen bond
hebi/searchI
donor. In RNA, uracil
d.do?chebiId
binds with a ribose
=17568)
sugar to form the
ChEMBL ChEMBL566
ribonucleoside
(https://ww
uridine. When a w.ebi.ac.uk/
phosphate attaches chembldb/i
to uridine, uridine 5′- ndex.php/c
monophosphate is ompound/in
produced.[6] spect/ChE
MBL566)
Uracil undergoes ChemSpi 1141 (htt
amide-imidic acid der ps://ww
tautomeric shifts w.chems

because any nuclear pider.co

m/Chemi
instability the
cal-Struc
molecule may have
ture.114
from the lack of
1.html)
formal aromaticity
DrugBan DB03419
is compensated by
k (https://
the cyclic-amidic
www.dru
stability.[5] The gbank.c
amide tautomer is a/drugs/
referred to as the DB0341
lactam structure, 9)
while the imidic acid ECHA 100.000.56
tautomer is referred InfoCard (https://ech
to as the lactim a.europa.e
structure. These u/substanc

tautomeric forms -informatio

n/-/substan
are predominant at
ceinfo/100.
pH 7. The lactam
000.565)
structure is the
EC 200-621-
most common form
Number 9
of uracil.
Gmelin 2896
Reference

IUPHAR/BPS
4560 (htt
Uracil tautomers: Amide or lactam
structure (left) and imide or lactim
structure (right)
p://www.
guidetop
Uracil also recycles
harmacol
itself to form
ogy.org/
nucleotides by GRAC/Li
undergoing a series gandDisp
of layForwa
phosphoribosyltrans rd?tab=s

ferase reactions.[2] ummary

&ligandId
Degradation of
=4560)
uracil produces the
KEGG C00106
substrates β-
(https://
alanine, carbon
www.keg
dioxide, and
g.jp/entr
ammonia.[2]
y/C0010
6)
C 4H 4N 2O 2→
− PubChem 1174 (htt
H3NCH2CH2COO
CID
+ ps://pub
+ NH4 + CO2
chem.nc
Oxidative bi.nlm.ni
degradation of h.gov/co
uracil produces urea
and maleic acid in mpound/
the presence of 1174)

H2O2 and Fe2+ or in RTECS YQ8650000

the presence of number

diatomic oxygen UNII 56HH86ZVC

and Fe2+. T (https://pre
cision.fda.go
Uracil is a weak v/uniisearc
acid. The first site of h/srs/unii/56
ionization of uracil HH86ZVC
is not known.[12] The T)

negative charge is CompTox DTXSID402

Dashboard
placed on the (EPA)
424 (https:/
oxygen anion and comptox.ep

produces a pKa of a.gov/dash

oard/chem
less than or equal to
12. The basic al/details/D
pKa = −3.4, while the XSID40214

acidic pKa = 9.389. 4)

In the gas phase, InChI

uracil has four sites InChI=1S/C4H4N2

O2/c7-3-1-2-5-
that are more acidic 4(8)6-3/h1-2H,
(H2,5,6,7,8)
than water.[13]
Key: ISAKRJDGNU
QOIC-UHFFFA
OYSA-N
In DNA
SMILES
lactam form: O=C
Uracil is rarely found
1C=CNC(=O)N
in DNA, and this 1
may have been an lactim form: Oc1n
ccc(O)n1
evolutionary change
Properties
to increase genetic
stability. This is
because cytosine Chemical C4H4N2O2
formula
can deaminate
spontaneously to Molar 112.08676

produce uracil mass g/mol

through hydrolytic Appeara Solid

deamination. nce

Therefore, if there Density 1.32

were an organism g/cm3

that used uracil in Melting 335 °C

its DNA, the point (635 °F;
deamination of 608 K)[1]

cytosine (which Boiling N/A –

undergoes base point decomposes

pairing with Solubility Soluble

in water
guanine) would lead
to formation of Hazards
uracil (which would Occupational safety
base pair with and health

adenine) during (OHS/OSH):

DNA synthesis. Main carcinogen

hazards
Uracil-DNA and
glycosylase excises teratogen

uracil bases from with

chronic
double-stranded
exposure
DNA. This enzyme
GHS labelling:
would therefore
recognize and cut Pictograms

out both types of Signal Warning

word
uracil – the one
incorporated Hazard H315,
statements
H319,
naturally, and the
one formed due to
cytosine H335,
deamination, which H361

would trigger Precautionary

P201, P20
statements
unnecessary and P261, P26

inappropriate repair P271, P28

P281,
processes.[14]
P302+P35
This problem is P304+P34

believed to have P305+P35

P338,
been solved in
P308+P31
terms of evolution,
P312, P32
that is by "tagging"
P332+P31
(methylating) uracil.
P337+P31
Methylated uracil is P362,
identical to thymine. P403+P23
Hence the P405, P50
hypothesis that, NFPA 1
1

over time, thymine 704

became standard in (fire dia

DNA instead of mond)

uracil. So cells Flash Non-

continue to use point flammable

uracil in RNA, and Related compounds

not in DNA, because Related Thymine

RNA is shorter-lived compounds
Cytosine
than DNA, and any Except where
potential uracil- otherwise noted,
data are given for
related errors do not materials in their
lead to lasting standard state (at
25 °C [77 °F],
damage. Apparently, 100 kPa).
either there was no verify (https://en.w
evolutionary ikipedia.org/w/inde
pressure to replace x.php?title=Special:
uracil in RNA with ComparePages&rev

the more complex 1=418274850&page

2=Uracil) (what is
thymine, or uracil
?)
has some chemical
Infobox references
property that is
useful in RNA, which
thymine lacks. Uracil-containing DNA still
exists, for example in

DNA of several phages[15]

Endopterygote development
Hypermutations during the synthesis of
vertebrate antibodies.
Synthesis

Biological

Organisms synthesize uracil, in the form of

uridine monophosphate (UMP), by
decarboxylating orotidine 5'-
monophosphate (orotidylic acid). In
humans this decarboxylation is achieved
by the enzyme UMP synthase. In contrast
to the purine nucleotides, the pyrimidine
ring (orotidylic acid) that leads uracil is
synthesized first and then linked to ribose
phosphate, forming UMP.[16]
Laboratory

There are many laboratory synthesis 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.[17]

Prebiotic

In 2009, NASA scientists reported having

produced uracil from pyrimidine and water
ice by exposing it to ultraviolet light under
space-like conditions.[10] This suggests a
possible natural original source for
uracil.[18] In 2014, NASA scientists
reported that additional complex DNA and
RNA organic compounds of life, including
uracil, cytosine and thymine, have been
formed in the laboratory under outer space
conditions, starting with ice, pyrimidine,
ammonia, and methanol, which are
compounds found in astrophysical
environments.[19] Pyrimidine, like
polycyclic aromatic hydrocarbons (PAHs),
a carbon-rich chemical found in the
Universe, may have been formed in red
giants or in interstellar dust and gas
clouds.[20]

Based on 12C/13C isotopic ratios of

organic compounds found in the
Murchison meteorite, it is believed that
uracil, xanthine, and related molecules can
also be formed extraterrestrially.[7] Data
from the Cassini mission, orbiting in the
Saturn system, suggests that uracil is
present in the surface of the moon Titan.[9]
In 2023, uracil was observed in a sample
from 162173 Ryugu, a near-Earth asteroid,
with no exposure to Earth's biosphere,
giving further evidence for synthesis in
space.[8]

Reactions

Chemical
structure of
uridine
Uracil readily undergoes regular reactions
including oxidation, nitration, and
alkylation. While in the presence of phenol
(PhOH) and sodium hypochlorite (NaOCl),
uracil can be visualized in ultraviolet
light.[5] Uracil also has the capability to
react with elemental halogens because of
the presence of more than one strongly
electron donating group.[5]

Uracil readily undergoes addition to ribose

sugars and phosphates to partake in
synthesis and further reactions in the
body. Uracil becomes uridine, uridine
monophosphate (UMP), uridine
diphosphate (UDP), uridine triphosphate
(UTP), and uridine diphosphate glucose
(UDP-glucose). Each one of these
molecules is synthesized in the body and
has specific functions.

When uracil reacts with anhydrous

hydrazine, a first-order kinetic reaction
occurs and the uracil ring opens up.[21] If
the pH of the reaction increases to > 10.5,
the uracil anion forms, making the reaction
go much more slowly. The same slowing
of the reaction occurs if the pH decreases,
because of the protonation of the
hydrazine.[21] The reactivity of uracil
remains unchanged, even if the
temperature changes.[21]
Uses
Uracil's use in the body is to help carry out
the synthesis of many enzymes necessary
for cell function through bonding with
riboses and phosphates.[2] Uracil serves as
allosteric regulator and coenzyme for
reactions in animals and in plants.[22] UMP
controls the activity of carbamoyl
phosphate synthetase and aspartate
transcarbamoylase in plants, while UDP
and UTP regulate CPSase II activity in
animals. UDP-glucose regulates the
conversion of glucose to galactose in the
liver and other tissues in the process of
carbohydrate metabolism.[22] Uracil is also
involved in the biosynthesis of
polysaccharides and the transportation of
sugars containing aldehydes.[22] Uracil is
important for the detoxification of many
carcinogens, for instance those found in
tobacco smoke.[23] Uracil is also required
to detoxify many drugs such as
cannabinoids (THC)[24] and morphine
(opioids).[25] It can also slightly increase
the risk for cancer in unusual cases in
which the body is extremely deficient in
folate.[26] The deficiency in folate leads to
increased ratio of deoxyuridine
monophosphates (dUMP)/deoxythymidine
monophosphates (dTMP) and uracil
misincorporation into DNA and eventually
low production of DNA.[26]

Uracil can be used for drug delivery and as

a pharmaceutical. When elemental fluorine
reacts with uracil, they produce 5-
fluorouracil. 5-Fluorouracil is an anticancer
drug (antimetabolite) used to masquerade
as uracil during the nucleic acid replication
process.[2] Because 5-fluorouracil is
similar in shape to, but does not undergo
the same chemistry as, uracil, the drug
inhibits RNA transcription enzymes,
thereby blocking RNA synthesis and
stopping the growth of cancerous cells.[2]
Uracil can also be used in the synthesis of
caffeine.[27] Uracil has also shown
potential as a HIV viral capsid inhibitor.[28]
Uracil derivatives have antiviral, anti-
tubercular and anti-leishmanial
activity.[29][30][31]

Uracil can be used to determine microbial

contamination of tomatoes. The presence
of uracil indicates lactic acid bacteria
contamination of the fruit.[32] Uracil
derivatives containing a diazine ring are
used in pesticides.[33] Uracil derivatives are
more often used as antiphotosynthetic
herbicides, destroying weeds in cotton,
sugar beet, turnips, soya, peas, sunflower
crops, vineyards, berry plantations, and
orchards.[33] Uracil derivatives can
enhance the activity of antimicrobial
polysaccharides such as chitosan.[34]

In yeast, uracil concentrations are

inversely proportional to uracil
permease.[35]

Mixtures containing uracil are also

commonly used to test reversed-phase
HPLC columns. As uracil is essentially
unretained by the non-polar stationary
phase, this can be used to determine the
dwell time (and subsequently dwell
volume, given a known flow rate) of the
system.
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External links
Uracil MS Spectrum (http://gmd.mpimp-
golm.mpg.de/Spectrums/b3fbd853-fbf6
-4ae3-aab2-e2fb5b212be3.aspx)

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