276:
201:
24:
523:
409:
534:
529:
The three forms frequently interchange so base-pairing properties can become altered at any time. The result of this is that during a subsequent round of replication a different base is aligned opposite the 5-BrU residue. Further rounds of replication 'fix' the change by incorporating a normal
545:
via base substitution. This base pair will change from an A-T to a G-C or from a G-C to an A-T after a number of replication cycles, depending on whether 5-BrU is within the DNA molecule or is an incoming base when it is enolized or ionized.
422:
560:
580:
IUPAC-IUB Commission on
Biochemical Nomenclature (1970). "Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents".
325:
511:, so it can be incorporated into DNA by aligning opposite adenine residues during DNA replication (see below left). Alternatively, the
618:
417:
290:
106:
429:
233:
196:
254:
158:
655:
271:
650:
489:
582:
645:
640:
242:
36:
178:
8:
72:
275:
200:
138:
82:
614:
609:
Griffiths, Anthony J.F.; Wessler, Susan R.; Carroll, Sean B.; Doebley, John (2012).
591:
348:
519:. This means that 5-BrU can be present in DNA either opposite adenine or guanine.
222:
579:
555:
542:
461:
400:
634:
481:
189:
23:
465:
595:
385:
169:
399:
Except where otherwise noted, data are given for materials in their
522:
500:
493:
477:
105:
516:
508:
485:
469:
209:
504:
457:
149:
608:
129:
95:
259:
512:
473:
299:
InChI=1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
533:
309:
InChI=1/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
503:
forms that have different base pairing properties. The
613:(10th ed.). New York: W.H. Freeman and Company.
515:(below right) and ion forms are complementary to
632:
507:form (shown in the infobox) is complementary to
221:
81:
530:nitrogen base into the complementary strand.
274:
199:
177:
241:
532:
484:. It is used mainly as an experimental
270:
633:
190:
302:Key: LQLQRFGHAALLLE-UHFFFAOYSA-N
157:
137:
488:, but its deoxyriboside derivative (
312:Key: LQLQRFGHAALLLE-UHFFFAOYAN
212:
13:
521:
14:
667:
611:Introduction to Genetic Analysis
456:) is a brominated derivative of
407:
369:
360:
22:
403:(at 25 °C , 100 kPa).
366:
58:5-Bromo-2,4-dihydroxypyrimidine
602:
573:
375:
354:
1:
566:
7:
549:
60:5-Bromopyrimidine-2,4-dione
10:
672:
397:
341:
321:
286:
65:
55:
35:
30:
21:
490:5-bromo-2-deoxy-uridine
41:5-Bromopyrimidine-2,4(1
538:
526:
499:5-BrU exists in three
541:Thus 5-BrU induces a
536:
525:
476:, and can induce DNA
37:Preferred IUPAC name
596:10.1021/bi00822a023
492:) is used to treat
480:in the same way as
468:, substituting for
393: g·mol
333:Br/C1=C/NC(=O)NC1=O
18:
539:
537:Mutagenesis by 5BU
527:
430:Infobox references
16:
620:978-1-4292-2943-2
590:(20): 4022–4027.
438:Chemical compound
436:
435:
255:CompTox Dashboard
107:Interactive image
663:
656:Pyrimidinediones
625:
624:
606:
600:
599:
577:
460:that acts as an
420:
414:
411:
410:
392:
377:
371:
368:
362:
356:
349:Chemical formula
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278:
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109:
85:
26:
19:
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621:
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578:
574:
569:
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439:
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425: ?)
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412:
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184:
164:
144:
123:
121:
112:
99:
88:
75:
61:
59:
51:
50:
12:
11:
5:
669:
659:
658:
653:
651:Organobromides
648:
643:
627:
626:
619:
601:
571:
570:
568:
565:
564:
563:
561:5-Chlorouracil
558:
556:5-Fluorouracil
551:
548:
543:point mutation
462:antimetabolite
437:
434:
433:
428:
406:
405:
401:standard state
398:
395:
394:
388:
382:
381:
378:
372:
363:
357:
352:
347:
344:
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339:
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280:
267:
265:
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249:
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194:
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174:
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166:
165:
163:
162:
154:
152:
146:
145:
143:
142:
134:
132:
126:
125:
118:
117:Abbreviations
114:
113:
111:
110:
102:
100:
93:
90:
89:
87:
86:
78:
76:
71:
68:
67:
63:
62:
57:
53:
52:
40:
39:
33:
32:
28:
27:
17:5-Bromouracil
9:
6:
4:
3:
2:
668:
657:
654:
652:
649:
647:
644:
642:
639:
638:
636:
622:
616:
612:
605:
597:
593:
589:
585:
584:
576:
572:
562:
559:
557:
554:
553:
547:
544:
535:
531:
524:
520:
518:
514:
510:
506:
502:
497:
495:
491:
487:
483:
482:2-aminopurine
479:
475:
471:
467:
463:
459:
455:
451:
447:
443:
442:5-Bromouracil
431:
424:
419:
402:
396:
389:
387:
384:
383:
353:
350:
346:
345:
340:
331:
330:
327:
320:
306:
296:
295:
292:
285:
277:
273:
272:DTXSID2058758
269:
268:
266:
256:
252:
251:
244:
240:
239:
237:
235:
232:
231:
224:
220:
219:
217:
211:
207:
206:
202:
198:
195:
193:
191:ECHA InfoCard
188:
187:
180:
176:
175:
173:
171:
168:
167:
160:
156:
155:
153:
151:
148:
147:
140:
136:
135:
133:
131:
128:
127:
119:
116:
115:
108:
104:
103:
101:
97:
92:
91:
84:
80:
79:
77:
74:
70:
69:
64:
54:
48:
44:
38:
34:
29:
25:
20:
646:Biomolecules
610:
604:
587:
583:Biochemistry
581:
575:
540:
528:
498:
453:
449:
445:
441:
440:
159:ChEMBL144730
66:Identifiers
56:Other names
46:
42:
641:Nucleobases
466:base analog
342:Properties
197:100.000.077
139:CHEBI:20552
635:Categories
567:References
501:tautomeric
386:Molar mass
243:4HK400G5UO
170:ChemSpider
94:3D model (
73:CAS Number
494:neoplasms
550:See also
478:mutation
517:guanine
509:adenine
486:mutagen
470:thymine
423:what is
421: (
391:190.984
210:PubChem
124:5BrUra
83:51-20-7
49:)-dione
617:
458:uracil
454:br5Ura
450:5BrUra
418:verify
415:
326:SMILES
150:ChEMBL
122:br5Ura
31:Names
452:, or
446:5-BrU
291:InChI
130:ChEBI
120:5-BrU
96:JSmol
615:ISBN
513:enol
505:keto
234:UNII
223:5802
179:5597
592:doi
474:DNA
472:in
464:or
260:EPA
213:CID
637::
586:.
496:.
448:,
367:Br
45:,3
623:.
598:.
594::
588:9
444:(
413:Y
379:2
376:O
373:2
370:N
364:3
361:H
358:4
355:C
262:)
258:(
98:)
47:H
43:H
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