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racil 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 references edit 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 1 2 3 4 5 6 7 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 1 2 3 4 5 6 brown dj evans rf cowden wb fenn md 1994 taylor ec ed the pyrimidines heterocyclic compounds vol 52 new york ny wiley isbn 978 0 471 50656 0 archived from the original on 12 may 2018 1 2 horton hr moran la ochs rs rawn dj scrimgeour kg 2002 principles of biochemistry 3rd ed upper saddle river nj prentice hall isbn 978 0 13 026672 9 1 2 martins z botta o fogel ml sephton ma glavin dp watson js et al 2008 extraterrestrial nucleobases in the murchison meteorite earth and planetary science letters 270 1 2 130 136 arxiv 0806 2286 bibcode 2008e psl 270 130m doi 10 1016 j epsl 2008 03 026 s2cid 14309508 1 2 oba y koga t takano y ogawa no ohkouchi n sasaki k et al 2023 uracil in the carbonaceous asteroid 162173 ryugu nature communications 14 1 1292 bibcode 2023natco 14 1292o doi 10 1038 s41467 023 36904 3 pmc 10030641 pmid 36944653 1 2 clark rn pearson n brown rh cruikshank dp barnes j jaumann r et al 2012 the surface composition of titan american astronomical society 44 201 02 bibcode 2012dps 4420102c 1 2 nuevo michel milam stefanie n sandford scott a elsila jamie e dworkin jason p 2009 formation of uracil from the ultraviolet photo irradiation of pyrimidine in pure h2o ices astrobiology 9 7 683 695 bibcode 2009asbio 9 683n doi 10 1089 ast 2008 0324 issn 1531 1074 pmid 19778279 madscinet the 24 hour exploding laboratory www madsci org archived from the original on 18 july 2005 zorbach ww tipson rs 1973 synthetic procedures in nucleic acid chemistry physical and physicochemical aids in determination of structure vol 2 new york ny wiley interscience isbn 978 0 471 98418 4 kurinovich ma lee jk august 2002 the acidity of uracil and uracil analogs in the gas phase four surprisingly acidic sites and biological implications journal of the american society for mass spectrometry 13 8 985 995 bibcode 2002jasms 13 985k doi 10 1016 s1044 0305 02 00410 5 pmid 12216739 békési a vértessy bg 2011 uracil in dna error or signal science in school 18 archived from the original on 23 march 2016 wang z mosbaugh dw march 1988 uracil dna glycosylase inhibitor of bacteriophage pbs2 cloning and effects of expression of the inhibitor gene in escherichia coli journal of bacteriology 170 3 1082 1091 doi 10 1128 jb 170 3 1082 1091 1988 pmc 210877 pmid 2963806 löffler monika zameitat elke 2004 pyrimidine biosynthesis encyclopedia of biological chemistry elsevier pp 600 605 doi 10 1016 b0 12 443710 9 00574 3 isbn 978 0 12 443710 4 chittenden gj schwartz aw september 1976 possible pathway for prebiotic uracil synthesis by photodehydrogenation 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of heterocycles in science technology medicine and agriculture new york ny john wiley and sons isbn 978 0 471 96034 8 vijayakumar balaji gowrivel ramesh deepthi manikandan k santhosh theresa mary sethumadhavan aiswarya priyadarisini v brindha radhakrishnan e k mani maheswaran kannan tharanikkarasu 2022 06 01 chitosan with pendant e 5 4 acetylphenyl diazenyl 6 aminouracil groups as synergetic antimicrobial agents journal of materials chemistry b 10 21 4048 4058 doi 10 1039 d2tb00240j issn 2050 7518 pmid 35507973 s2cid 248526212 séron k blondel mo haguenauer tsapis r volland c march 1999 uracil induced down regulation of the yeast uracil permease journal of bacteriology 181 6 1793 1800 doi 10 1128 jb 181 6 1793 1800 1999 pmc 93577 pmid 10074071 external links edit uracil ms spectrum v t e nucleic acid constituents nucleobase purine adenine guanine hypoxanthine xanthine purine analogue pyrimidine uracil thymine cytosine pyrimidine analogue unnatural base pair ubp nucleoside ribonucleoside adenosine guanosine 5 methyluridine uridine 5 methylcytidine cytidine pseudouridine inosine n 6 methyladenosine xanthosine wybutosine deoxyribonucleoside deoxyadenosine deoxyguanosine thymidine deoxyuridine deoxycytidine deoxyinosine deoxyxanthosine nucleotide nucleoside monophosphate ribonucleotide amp gmp m 5 ump ump cmp imp xmp deoxyribonucleotide damp dgmp dtmp dump dcmp dimp dxmp cyclic nucleotide camp cgmp c di gmp c di amp cadpr cgamp nucleoside diphosphate adp gdp m 5 udp udp cdp xanthosine diphosphate dadp dgdp dtdp dudp dcdp nucleoside triphosphate atp gtp m 5 utp utp ctp itp xtp datp dgtp dttp dutp dctp ditp dxtp v t e purine receptor modulators receptor ligands p0 adenine agonists 8 aminoadenine adenine p1 adenosine agonists 2 1 hexynyl n methyladenosine 2 cl ib meca 2 chloroadenosine 2 meccpa 4 o β d glucosyl 9 o 6 deoxysaccharosyl olivil 5 n ethylcarboxamidoadenosine adenosine adp amp apadenoson atl 146e atp bay 60 6583 binodenoson capadenoson cgs 21680 cp 532 903 cv 1808 evodenoson gr 79236 heneca luf 5835 luf 5845 n 6 cyclopentyladenosine namodenoson neca neladenoson dalanate piclidenoson regadenoson sdz wag 994 selodenoson sonedenoson tecadenoson trabodenoson uk 432 097 yzg 331 antagonists 3 chlorostyrylcaffeine csc 7 methylxanthine 8 chlorotheophylline 8 phenyl 1 3 dipropylxanthine 8 phenyltheophylline acefylline aminophylline atl 444 azd 4635 bamifylline cafedrine caffeine caffeine citrate cartazolate cgh 2466 cgs 15943 choline theophyllinate ciforadenant cpx cvt 6883 dimethazan dmpx dpcpx dyphylline enprofylline etazolate etrumadenant fenethylline ibmx imaradenant inupadenant isam 140 isam r316 isovaleric acid istradefylline kf 26777 lu aa41063 lu aa47070 mre3008f20 mrs 1191 mrs 1220 mrs 1334 mrs 1523 mrs 1706 mrs 1754 mrs 3777 msx 2 msx 3 msx 4 muvadenant paraxanthine pentoxifylline preladenant propentofylline proxyphylline psb 10 psb 11 psb 36 psb 603 psb 788 psb 1115 psb 1901 reversine rolofylline sch 442 416 sch 58261 sipagladenant taminadenant theacrine theobromine theodrenaline theophylline tozadenant tracazolate vipadenant vuf 5574 zm 241 385 p2 nucleotide p2x atp tooltip adenosine triphosphate agonists 2 me satp α β me atp adenosine adp amp ap4a ap5a atp atpγs bzatp cibacron blue ctp d β γ me atp gtp ht amp ivermectin l β γ me atp mrs 2219 papet atp utp zinc antagonists 5 bdbd a 317491 a 438079 a 740003 a 804598 a 839977 af 353 az 10606120 az 11645373 bbg calcium calmidazolium chelerythrine copper emodin rheum officinale evans blue gefapixant gw 791343 hma ip5i isoppads jnj 47965567 kn 04 kn 62 magnesium mrs 2159 nf 023 nf 110 nf 157 nf 279 nf 449 opiranserin vvz 149 oxidized atp phenol red phenolphthalein ppads ppnds psb 12062 puerarin radix puerariae purotoxin 1 rb 2 ro 0437626 ro 51 ro 3 sodium ferulate angelica sinensis ligusticum wallichii suramin tc p 262 tetramethylpyrazine ligustrazine ligusticum wallichii tnp atp zinc p2y agonists 2 me sadp 2 me satp 2 thio utp 5 br udp 5 ome udp α β me atp adenosine adp adpβs ap3a ar c 67085mx atp atpγs ctp datp denufosol diquafosol idp itp ins 365 ins 37217 mrs 2365 mrs 2690 mrs 2693 mrs 2768 mrs 2957 mrs 4062 nf 546 papet atp psb 0474 psb 1114 udp udpβs udp galactose udp glucose udp n acetylglucosamine up3u utp utpγs antagonists 2 me samp a3p5ps ampαs ap4a ar c 66096 ar c 67085mx ar c 69931mx ar c 118925xx atp bzatp c1330 7 cangrelor clopidogrel elinogrel ip5i mrs 2179 mrs 2211 mrs 2279 mrs 2395 mrs 2500 mrs 2578 nf 157 nf 340 pit ppads prasugrel psb 0739 rb 2 regrelor suramin ticagrelor ticlopidine udp transporter blockers cnts tooltip concentrative nucleoside transporters 6 hydroxy 7 methoxyflavone adenosine dmethpmr estradiol kgo 2142 kgo 2173 methpmr phloridzin progesterone ents tooltip equilibrative nucleoside transporters barbiturates benzodiazepines cilostazol dilazep dipyridamole estradiol ethanol hexobendine nbmpr pentoxifylline progesterone propentofylline pmat tooltip plasma membrane monoamine transporter decynium 22 enzyme inhibitors xo tooltip xanthine oxidase allopurinol amflutizole benzbromarone caffeic acid cinnamaldehyde cinnamomum osmophloeum febuxostat myo inositol kaempferol myricetin niraxostat oxipurinol phytic acid pistacia integerrima propolis quercetin tisopurine topiroxostat others aminopterin azathioprine methotrexate mycophenolic acid pemetrexed pralatrexate many others others precursors adenine adenosine amp adp atp cytosine cytidine cmp cdp ctp guanine guanosine gmp gdp gtp hypoxanthine inosine imp idp itp ribose uracil uridine ump udp utp others chrysophanol rhubarb see also receptor signaling modulators authority control databases international gnd national united states israel other yale lux retrieved from https en wikipedia org w index php title uracil oldid 1369491569 categories nucleobases uracil derivatives acylureas hidden categories articles with short description short description is different from wikidata chemical articles with multiple compound ids multiple chemicals in an infobox that need indexing article...