504:
83:
450:
535:
493:
269:
75:
522:
482:
406:
384:
437:
395:
548:
424:
40:
165:, with the bases A, G, C, and T being found in DNA while A, G, C, and U are found in RNA. Thymine and uracil are distinguished by merely the presence or absence of a methyl group on the fifth carbon (C5) of these heterocyclic six-membered rings. In addition, some viruses have
602:
are used as anticancer and antiviral agents. The viral polymerase incorporates these compounds with non-canonical bases. These compounds are activated in the cells by being converted into nucleotides; they are administered as
1368:
658:. Nam et al. demonstrated the direct condensation of nucleobases with ribose to give ribonucleosides in aqueous microdroplets, a key step leading to RNA formation. Similar results were obtained by Becker et al.
305:) create the "backbone" strands for a single- or double helix biomolecule. In the double helix of DNA, the two strands are oriented chemically in opposite directions, which permits base pairing by providing
272:
Chemical structure of DNA, showing four nucleobase pairs produced by eight nucleotides: adenine (A) is joined to thymine (T), and guanine (G) is joined to cytosine (C). + This structure also shows the
220:, connect the two strands of the helix and are often compared to the rungs of a ladder. Only pairing purine with pyrimidine ensures a constant width for the DNA. The A–T pairing is based on two
1735:
1361:
1280:
Becker, Sidney; Feldmann, Jonas; Wiedemann, Stefan; Okamura, Hidenori; Schneider, Christina; Iwan, Katharina; Crisp, Antony; Rossa, Martin; Amatov, Tynchtyk; Carell, Thomas (2019).
1354:
293:
At the sides of nucleic acid structure, phosphate molecules successively connect the two sugar-rings of two adjacent nucleotide monomers, thereby creating a long chain
363:(replacement of the amine-group with a carbonyl-group). Hypoxanthine is produced from adenine, xanthine from guanine, and uracil results from deamination of cytosine.
325:
DNA and RNA also contain other (non-primary) bases that have been modified after the nucleic acid chain has been formed. In DNA, the most common modified base is
643:. Molecules as complex as RNA must have arisen from small molecules whose reactivity was governed by physico-chemical processes. RNA is composed of
571:
A vast number of nucleobase analogues exist. The most common applications are used as fluorescent probes, either directly or indirectly, such as
214:
DNA comprises a purine and a pyrimidine: either an A paired with a T or a C paired with a G. These purine-pyrimidine pairs, which are called
503:
1341:
306:
215:
274:
199:), at the C6 carbon in adenine and C2 in guanine. Similarly, the simple-ring structure of cytosine, uracil, and thymine is derived of
742:
607:
as charged nucleotides cannot easily cross cell membranes. At least one set of new base pairs has been announced as of May 2014.
449:
534:
492:
1715:
1710:
758:
405:
521:
1853:
1667:
1662:
481:
260:, but those properties are not especially important for understanding most of the biological functions of nucleobases.
1891:
1886:
1682:
1906:
1802:
1797:
1692:
1687:
1677:
1624:
383:
1916:
1817:
1769:
588:
1911:
1901:
1644:
436:
314:
1812:
1873:
1831:
1784:
1672:
1619:
1614:
592:
508:
257:
1896:
1848:
1843:
1634:
394:
970:
1863:
1807:
1764:
1759:
1629:
685:
679:
572:
566:
423:
130:
852:
Callahan MP, Smith KE, Cleaves HJ, Ruzicka J, Stern JC, Glavin DP, House CH, Dworkin JP (August 2011).
916:
1941:
1868:
1858:
1779:
1581:
1296:
1234:
1177:
1020:
869:
682: – Universal notation using the Roman characters A, C, G, and T to call the four DNA nucleotides
1774:
1654:
1543:
1446:
599:
579:. Several groups are working on alternative "extra" base pairs to extend the genetic code, such as
1576:
1281:
1520:
1320:
942:
619:, knowledge is required of chemical pathways that permit formation of the key building blocks of
1164:
Malyshev DA, Dhami K, Lavergne T, Chen T, Dai N, Foster JM, Corrêa IR, Romesberg FE (May 2014).
82:
1730:
1702:
1312:
1262:
1203:
1146:
1097:
1048:
897:
738:
486:
454:
342:
289:
the strand on the right. The strands twist around each other to form a double helix structure.
244:
166:
224:, while the C–G pairing is based on three. In both cases, the hydrogen bonds are between the
1500:
1304:
1252:
1242:
1193:
1185:
1136:
1128:
1087:
1079:
1038:
1028:
887:
877:
834:
781:
730:
539:
497:
326:
252:
177:
126:
1490:
1419:
636:
410:
329:(mC). In RNA, there are many modified bases, including those contained in the nucleosides
310:
74:
1300:
1282:"Unified prebiotically plausible synthesis of pyrimidine and purine RNA ribonucleotides"
1238:
1181:
1024:
873:
1606:
1556:
1551:
1472:
1257:
1222:
1198:
1165:
1141:
1116:
892:
853:
801:"Section 25.2, Purine Bases Can Be Synthesized de Novo or Recycled by Salvage Pathways"
632:
526:
334:
268:
1092:
1067:
994:
125:
and to stack one upon another leads directly to long-chain helical structures such as
1935:
1725:
1720:
1639:
1571:
1510:
1324:
1223:"Abiotic synthesis of purine and pyrimidine ribonucleosides in aqueous microdroplets"
1043:
1008:
651:
nucleotides, both of which are necessary for reliable information transfer, and thus
552:
330:
221:
118:
55:
1951:
1946:
1566:
1409:
1377:
1007:
Nguyen T, Brunson D, Crespi CL, Penman BW, Wishnok JS, Tannenbaum SR (April 1992).
947:
388:
348:
240:
162:
670: – Any of several glycosylamines comprising a nucleobase and a sugar molecule
17:
995:"Role of 5' mRNA and 5' U snRNA cap structures in regulation of gene expression"
624:
616:
584:
576:
360:
302:
294:
189:
106:
1013:
Proceedings of the
National Academy of Sciences of the United States of America
858:
Proceedings of the
National Academy of Sciences of the United States of America
826:
800:
773:
1595:
1533:
1528:
1463:
1426:
1386:
1068:"A third base pair for the polymerase chain reaction: inserting isoC and isoG"
854:"Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases"
673:
667:
648:
604:
580:
441:
277:
of each of the two phosphate-deoxyribose backbones, or strands. The 5' to 3' (
200:
110:
1561:
1485:
1480:
1453:
1346:
1308:
1247:
882:
838:
785:
734:
655:
652:
628:
247:, and 6,8-diaminopurine may have formed in outer space as well as on earth.
122:
44:
1316:
1266:
1207:
1150:
1101:
1033:
901:
547:
39:
1052:
707:
30:"ACGT" redirects here. For the Japanese animation production company, see
1505:
1441:
1414:
1132:
1083:
1009:"DNA damage and mutation in human cells exposed to nitric oxide in vitro"
399:
352:
236:
229:
138:
102:
1189:
1117:"Fluorescent probing for RNA molecules by an unnatural base-pair system"
471:
373:
1515:
1495:
1436:
1404:
1399:
759:"Some viruses thwart bacterial defenses with a unique genetic alphabet"
639:. These were the fundamental molecules that combined in series to form
428:
356:
338:
146:
142:
134:
114:
31:
1431:
1394:
644:
298:
181:
150:
1066:
Johnson SC, Sherrill CB, Marshall DJ, Moser MJ, Prudent JR (2004).
1115:
Kimoto M, Mitsui T, Harada Y, Sato A, Yokoyama S, Hirao I (2007).
943:"DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests"
225:
211:
170:
188:. The purine nitrogenous bases are characterized by their single
1342:
Base pairing in DNA Double Helix (shows specific hydrogen bonds)
920:
865:
725:
Soukup, Garrett A. (2003). "Nucleic Acids: General
Properties".
620:
1350:
825:
772:
706:
469:
These are examples of modified cytidine, thymidine or uridine.
640:
27:
Nitrogen-containing biological compounds that form nucleosides
1166:"A semi-synthetic organism with an expanded genetic alphabet"
917:"NASA Researchers: DNA Building Blocks Can Be Made in Space"
47:
are produced by four nucleotide monomers, nucleobases are
676: – Biological molecules constituting nucleic acids
371:
These are examples of modified adenosine or guanosine.
169:(Z) instead of adenine. It differs in having an extra
1830:
1748:
1701:
1653:
1605:
1594:
1542:
1471:
1462:
1385:
1221:Nam, Inho; Nam, Hong Gil; Zare, Richard N. (2018).
688: – Succession of nucleotides in a nucleic acid
309:between the two bases, and which is essential for
611:Prebiotic condensation of nucleobases with ribose
256:reflects these compounds' chemical properties in
86:Pyrimidine nucleobases are simple ring molecules.
161:. They function as the fundamental units of the
1227:Proceedings of the National Academy of Sciences
297:. These chain-joins of phosphates with sugars (
173:group, creating a more stable bond to thymine.
51:. Guanine (G) is paired with cytosine (C) via
1362:
8:
513:
473:
415:
375:
78:Purine nucleobases are fused-ring molecules.
62:. Adenine (A) is paired with uracil (U) via
210:Each of the base pairs in a typical double-
105:-containing biological compounds that form
1836:
1752:
1602:
1468:
1369:
1355:
1347:
575:, which are used to label cRNA or cDNA in
355:are two of the many bases created through
117:constituting the basic building blocks of
1256:
1246:
1197:
1140:
1091:
1042:
1032:
891:
881:
317:of the encoded information found in DNA.
997:– Research – Retrieved 13 December 2010.
267:
195:
81:
73:
38:
698:
281:"5 prime to 3 prime") directions are:
235:Nucleobases such as adenine, guanine,
203:, so those three bases are called the
121:. The ability of nucleobases to form
7:
941:ScienceDaily Staff (9 August 2011).
109:, which, in turn, are components of
915:Steigerwald, John (8 August 2011).
827:"IUPAC - pyrimidine bases (P04958)"
708:"IUPAC - nucleotide bases (N04254)"
232:groups on the complementary bases.
25:
799:Berg JM, Tymoczko JL, Stryer L.
546:
533:
520:
502:
491:
480:
448:
435:
422:
404:
393:
382:
774:"IUPAC - purine bases (P04953)"
465:Modified pyrimidine nucleobases
359:presence, both of them through
180:skeletal structure derived of
1:
285:the strand on the left, and
729:. American Cancer Society.
589:2-amino-6-(2-thienyl)purine
367:Modified purine nucleobases
176:Adenine and guanine have a
1968:
1599:(Nucleoside monophosphate)
631:hypothesis, free-floating
564:
29:
1882:
1839:
1793:
1755:
1454:Unnatural base pair (UBP)
805:Biochemistry. 5th Edition
184:, hence they are called
133:(DNA). Five nucleobases—
1832:Nucleoside triphosphate
1309:10.1126/science.aax2747
1248:10.1073/pnas.1718559115
971:"BIOL2060: Translation"
883:10.1073/pnas.1106493108
839:10.1351/goldbook.p04958
786:10.1351/goldbook.p04953
735:10.1038/npg.els.0001335
615:In order to understand
509:5-Hydroxymethylcytosine
250:The origin of the term
1785:Xanthosine diphosphate
1749:Nucleoside diphosphate
1121:Nucleic Acids Research
1072:Nucleic Acids Research
1034:10.1073/pnas.89.7.3030
593:pyrrole-2-carbaldehyde
561:Artificial nucleobases
290:
87:
79:
71:
686:Nucleic acid sequence
680:Nucleic acid notation
598:In medicine, several
573:aminoallyl nucleotide
567:Nucleic acid analogue
271:
131:deoxyribonucleic acid
85:
77:
42:
635:were present in the
625:prebiotic conditions
600:nucleoside analogues
321:Modified nucleobases
113:, with all of these
1655:Deoxyribonucleotide
1544:Deoxyribonucleoside
1447:Pyrimidine analogue
1301:2019Sci...366...76B
1239:2018PNAS..115...36N
1190:10.1038/nature13314
1182:2014Natur.509..385M
1025:1992PNAS...89.3030N
874:2011PNAS..10813995C
627:. According to the
587:or the fluorescent
258:acid–base reactions
1133:10.1093/nar/gkm508
1084:10.1093/nar/gkh522
969:Stavely, Brian E.
831:goldbook.iupac.org
778:goldbook.iupac.org
712:goldbook.iupac.org
291:
88:
80:
72:
43:Base pairing: Two
1929:
1928:
1925:
1924:
1826:
1825:
1744:
1743:
1703:Cyclic nucleotide
1590:
1589:
558:
557:
487:5,6-Dihydrouracil
462:
461:
455:7-Methylguanosine
343:7-methylguanosine
245:2,6-diaminopurine
99:nitrogenous bases
18:Nitrogenous bases
16:(Redirected from
1959:
1837:
1753:
1603:
1524:-Methyladenosine
1501:5-Methylcytidine
1469:
1371:
1364:
1357:
1348:
1329:
1328:
1286:
1277:
1271:
1270:
1260:
1250:
1218:
1212:
1211:
1201:
1161:
1155:
1154:
1144:
1112:
1106:
1105:
1095:
1063:
1057:
1056:
1046:
1036:
1004:
998:
992:
986:
985:
983:
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966:
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959:
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822:
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811:
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790:
789:
769:
763:
762:
755:
749:
748:
722:
716:
715:
703:
623:under plausible
550:
540:5-Methylcytidine
537:
524:
506:
498:5-Methylcytosine
495:
484:
472:
452:
439:
426:
408:
397:
386:
374:
327:5-methylcytosine
217:base complements
205:pyrimidine bases
198:
127:ribonucleic acid
91:Nucleotide bases
66:hydrogen bonds,
21:
1967:
1966:
1962:
1961:
1960:
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1956:
1932:
1931:
1930:
1921:
1878:
1822:
1789:
1740:
1697:
1649:
1598:
1586:
1582:Deoxyxanthosine
1538:
1491:5-Methyluridine
1458:
1420:Purine analogue
1381:
1375:
1338:
1333:
1332:
1295:(6461): 76–82.
1284:
1279:
1278:
1274:
1220:
1219:
1215:
1176:(7500): 385–8.
1163:
1162:
1158:
1127:(16): 5360–69.
1114:
1113:
1109:
1065:
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1060:
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1005:
1001:
993:
989:
979:
977:
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723:
719:
705:
704:
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695:
664:
637:primordial soup
633:ribonucleotides
613:
569:
563:
551:
542:
538:
529:
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496:
485:
467:
457:
453:
444:
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431:
427:
411:7-Methylguanine
409:
398:
387:
369:
323:
307:complementarity
266:
197:
193:
153:(U)—are called
35:
28:
23:
22:
15:
12:
11:
5:
1965:
1963:
1955:
1954:
1949:
1944:
1934:
1933:
1927:
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1923:
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1920:
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1904:
1899:
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1889:
1883:
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1607:Ribonucleotide
1600:
1592:
1591:
1588:
1587:
1585:
1584:
1579:
1574:
1569:
1564:
1559:
1557:Deoxyguanosine
1554:
1552:Deoxyadenosine
1548:
1546:
1540:
1539:
1537:
1536:
1531:
1526:
1518:
1513:
1508:
1503:
1498:
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1488:
1483:
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1473:Ribonucleoside
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1336:External links
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1078:(6): 1937–41.
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617:how life arose
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565:Main article:
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527:Dihydrouridine
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335:dihydrouridine
322:
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275:directionality
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222:hydrogen bonds
56:hydrogen bonds
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1572:Deoxycytidine
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1511:Pseudouridine
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1019:(7): 3030–4.
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761:. 5 May 2021.
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553:Pseudouridine
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331:pseudouridine
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315:transcription
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119:nucleic acids
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33:
19:
1577:Deoxyinosine
1567:Deoxyuridine
1521:
1410:Hypoxanthine
1380:constituents
1378:Nucleic acid
1292:
1288:
1275:
1233:(1): 36–40.
1230:
1226:
1216:
1173:
1169:
1159:
1124:
1120:
1110:
1075:
1071:
1061:
1016:
1012:
1002:
990:
978:. Retrieved
974:
964:
952:. Retrieved
948:ScienceDaily
946:
936:
924:. Retrieved
910:
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808:. Retrieved
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614:
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515:
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417:
389:Hypoxanthine
377:
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349:Hypoxanthine
347:
324:
292:
286:
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278:
251:
249:
241:hypoxanthine
234:
216:
209:
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186:purine bases
185:
175:
167:aminoadenine
163:genetic code
158:
154:
98:
94:
90:
89:
67:
63:
59:
52:
48:
36:
1942:Nucleobases
868:: 13995–8.
810:11 December
605:nucleosides
585:isocytosine
577:microarrays
361:deamination
311:replication
303:deoxyribose
295:biomolecule
190:amino group
111:nucleotides
107:nucleosides
95:nucleobases
1936:Categories
1596:Nucleotide
1534:Wybutosine
1529:Xanthosine
1464:Nucleoside
1427:Pyrimidine
1387:Nucleobase
975:www.mun.ca
693:References
674:Nucleotide
668:Nucleoside
649:pyrimidine
581:isoguanine
516:Nucleoside
476:Nucleobase
442:Xanthosine
418:Nucleoside
378:Nucleobase
243:, purine,
201:pyrimidine
178:fused-ring
129:(RNA) and
123:base pairs
45:base pairs
1562:Thymidine
1486:Guanosine
1481:Adenosine
1325:203719976
980:17 August
926:10 August
656:evolution
653:Darwinian
629:RNA world
341:(I), and
264:Structure
159:canonical
149:(T), and
1726:c-di-AMP
1721:c-di-GMP
1506:Cytidine
1442:Cytosine
1415:Xanthine
1317:31604305
1267:29255025
1208:24805238
1151:17693436
1102:15051811
954:9 August
902:21836052
662:See also
400:Xanthine
353:xanthine
237:xanthine
230:carbonyl
139:cytosine
115:monomers
103:nitrogen
1516:Inosine
1496:Uridine
1437:Thymine
1405:Guanine
1400:Adenine
1297:Bibcode
1289:Science
1258:5776833
1235:Bibcode
1199:4058825
1178:Bibcode
1142:2018647
1053:1557408
1021:Bibcode
893:3161613
870:Bibcode
429:Inosine
357:mutagen
339:inosine
155:primary
147:thymine
143:guanine
135:adenine
49:in blue
32:A.C.G.T
1432:Uracil
1395:Purine
1323:
1315:
1265:
1255:
1206:
1196:
1170:Nature
1149:
1139:
1100:
1093:390373
1090:
1051:
1041:
900:
890:
864:(34).
741:
645:purine
345:(mG).
313:of or
299:ribose
182:purine
151:uracil
101:) are
93:(also
68:in red
60:in red
1736:cGAMP
1731:cADPR
1321:S2CID
1285:(PDF)
1044:48797
337:(D),
333:(Ψ),
226:amine
212:helix
171:amine
145:(G),
141:(C),
137:(A),
53:three
1917:dXTP
1912:dITP
1907:dCTP
1902:dUTP
1897:dTTP
1892:dGTP
1887:dATP
1854:mUTP
1818:dCDP
1813:dUDP
1808:dTDP
1803:dGDP
1798:dADP
1770:mUDP
1716:cGMP
1711:cAMP
1693:dXMP
1688:dIMP
1683:dCMP
1678:dUMP
1673:dTMP
1668:dGMP
1663:dAMP
1625:mUMP
1313:PMID
1263:PMID
1204:PMID
1147:PMID
1098:PMID
1049:PMID
982:2020
956:2011
928:2011
921:NASA
898:PMID
866:PNAS
812:2019
739:ISBN
647:and
621:life
591:and
583:and
351:and
283:down
279:read
253:base
228:and
1952:RNA
1947:DNA
1874:XTP
1869:ITP
1864:CTP
1859:UTP
1849:GTP
1844:ATP
1780:CDP
1775:UDP
1765:GDP
1760:ADP
1645:XMP
1640:IMP
1635:CMP
1630:UMP
1620:GMP
1615:AMP
1305:doi
1293:366
1253:PMC
1243:doi
1231:115
1194:PMC
1186:doi
1174:509
1137:PMC
1129:doi
1088:PMC
1080:doi
1039:PMC
1029:doi
888:PMC
878:doi
862:108
835:doi
782:doi
731:doi
727:eLS
641:RNA
458:mG
301:or
194:−NH
157:or
64:two
1938::
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1123:.
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803:.
780:.
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737:.
710:.
595:.
543:mC
287:up
239:,
207:.
97:,
58:,
1522:N
1370:e
1363:t
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880::
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733::
714:.
530:D
445:X
432:I
196:2
192:(
70:.
34:.
20:)
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