467:
31:
542:
692:
733:
techniques are then used to read the sequence of the bisulfite-treated DNA. Those cytosines that are read as cytosines after sequencing represent methylated cytosines, while those that are read as thymines represent unmethylated cytosines in the genomic DNA.
572:. This reaction is useful for the separation and purification of aldehydes. The bisulfite adducts are charged and so are more soluble in polar solvents. The reaction can be reversed in base or strong acid. Examples of such procedures are described for
235:
836:
639:. Sodium bisulfite is a decoloration agent in purification procedures because it reduces strongly coloured oxidizing agents, conjugated alkenes and carbonyl compounds.
173:
There exist two tautomers of bisulfite. They interconvert readily but can be characterized individually by various spectroscopic methods. They have been observed by
459:
Because of this equilibrium, anhydrous sodium and potassium salts of bisulfite cannot be obtained. However, there are some reports of anhydrous bisulfites with large
896:
Carter, Kay L.; Siddiquee, Tasneem A.; Murphy, Kristen L.; Bennett, Dennis W. (18 March 2004). "The surprisingly elusive crystal structure of sodium metabisulfite".
143:. One tautomer has the proton attached to one of the three oxygen centers. In the second tautomer the proton resides on sulfur. The S-protonated tautomer has
177:
769:
853:
807:
670:
1232:
Frommer, M.; McDonald, L. E.; Millar, D. S.; Collis, C. M.; Watt, F.; Grigg, G. W.; Molloy P. L.; Paul, C. L. (1992).
1234:"A genomic sequencing protocol that yields a positive display of 5-methylcytosine residues in individual DNA strands"
834:
Barberá, José Jiménez; Metzger, Adolf; Wolf, Manfred (2000). "Sulfites, Thiosulfates, and
Dithionitesl Chemistry".
328:
726:
531:, sodium bisulfite is used to reduce the residual 'chlorine' which can have a negative impact on aquatic life.
389:
Attempted isolation of the common salts of bisulfite results in dehydration of the anion with formation of
636:
190:
761:
541:
1303:
1247:
686:
245:
79:
1196:
Dauben, Hyp J. Jr.; Ringold, Howard J.; Wade, Robert H.; Pearson, David L.; Anderson, Arthur G. Jr.
1298:
658:
600:, the bisulfite reaction is reported to allow differentiation between the primary reaction product
961:"Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol"
869:
Maylor, R.; Gill, J. B.; Goodall, D. C. (July 1971). "Some studies on anhydrous cobalt sulphite".
466:
528:
144:
959:
Furigay, Maxwell H.; Boucher, Maria M.; Mizgier, Nikola A.; Brindle, Cheyenne S. (2018-04-02).
1275:
1202:
1174:
1146:
1118:
1090:
1062:
1045:
1022:
994:
976:
937:
913:
849:
765:
662:
643:
632:
549:
729:, the uracil is amplified as thymine and the methylated cytosines are amplified as cytosine.
695:
The chemical reaction that underlies the bisulfite-mediated conversion of cytosine to uracil.
1265:
1255:
1207:
984:
968:
905:
878:
841:
816:
753:
719:
674:
628:
553:
1013:
30:
1251:
989:
960:
730:
608:
601:
480:
302:
298:
260:
1292:
1270:
1233:
882:
593:
569:
565:
390:
78:
ion are also known as "sulfite lyes". Sodium bisulfite is used interchangeably with
624:
585:
573:
24:
691:
1197:
1169:
1141:
1113:
1085:
1049:
1017:
932:
786:
700:
666:
577:
460:
1084:
Soffer, M. D.; Bellis, M. P.; Gellerson, Hilda E.; Stewart, Roberta A. (1963).
909:
524:
520:
1211:
980:
845:
174:
20:
1260:
998:
917:
1279:
722:, a methylated form of cytosine with a methyl group attached to carbon 5.
711:
650:
647:
612:
561:
140:
35:
820:
616:
597:
589:
338:
715:
620:
581:
557:
94:). Sodium metabisulfite dissolves in water to give a solution of Na
972:
931:
Young, Steven D.; Buse, Charles T.; Heathcock, Clayton H. (1990).
787:"Equilibrium quotient for the isomerization of bisulfite ion from
690:
654:
465:
47:
29:
1238:
519:
Its reducing properties are exploited to precipitate gold from
704:
259:
Solutions of bisulfite are typically prepared by treatment of
607:
Another use of bisulfite in organic chemistry is as a mild
139:
The bisulfite anion exists in solution as a mixture of two
209:
193:
898:
611:, for example to remove traces or excess amounts of
229:
216:
215:
725:When the bisulfite-treated DNA is amplified via
699:Sodium bisulfite is used in the analysis of the
527:) and reduce chromium(VI) to chromium(III). In
710:In this technique, sodium bisulfite deaminates
470:Structure of disulfite (aka metabisulfite) ion.
837:Ullmann's Encyclopedia of Industrial Chemistry
8:
642:Bisulfite is also the key ingredient in the
933:"2-Methyl-2-(Trimethylsiloxy)pentan-3-one"
871:Journal of Inorganic and Nuclear Chemistry
1269:
1259:
1168:Ronzio, Anthony R.; Waugh, T. D. (1955).
988:
748:
746:
677:that uses sodium bisulfite as a reagent.
217:
210:
208:
199:
197:
195:
194:
192:
661:. The first step in this reaction is an
653:group is converted to the corresponding
604:and the main contaminant cyclooctanone.
483:agent, especially for oxygen scrubbing:
1112:Russell, Alfred; Kenyon, R. L. (1955).
742:
200:
785:Horner, D. A.; Connick, R. E. (1986).
153:. The O-protonated tautomer has only
34:Equilibrium reaction relating the two
230:{\displaystyle {\ce {<=>>}}}
7:
592:. In the ring-expansion reaction of
665:of sodium bisulfite to an aromatic
198:
1058:-Dimethylamino)phenylacetonitrile"
14:
965:Journal of Visualized Experiments
540:
385:Dehydration/hydration equilibria
337:of 6.97. Its conjugate base is
327:is a weak acidic species with a
218:
201:
1:
568:. These adducts are α-hydroxy
883:10.1016/0022-1902(71)80558-4
671:Bucherer carbazole synthesis
414:), also known as disulfite:
1018:"2-Methyl-3-phenylpropanal"
50:-recommended nomenclature:
1320:
1220:, vol. 4, p. 221
1184:, vol. 3, p. 438
1156:, vol. 4, p. 467
1128:, vol. 3, p. 747
1100:, vol. 4, p. 903
1072:, vol. 5, p. 437
1032:, vol. 7, p. 361
947:, vol. 7, p. 381
684:
18:
1140:Cornforth, J. W. (1963).
910:10.1107/S0108768104003325
758:Chemistry of the Elements
756:; Earnshaw, Alan (1997).
727:polymerase chain reaction
1212:10.15227/orgsyn.034.0019
846:10.1002/14356007.a25_477
681:Bisulfite DNA sequencing
66:. Salts containing the
19:Not to be confused with
16:Chemical compound or ion
840:. Weinheim: Wiley-VCH.
703:status of cytosines in
1261:10.1073/pnas.89.5.1827
718:, but does not affect
696:
646:. In this reaction an
637:potassium permanganate
471:
231:
39:
762:Butterworth-Heinemann
754:Greenwood, Norman N.
694:
685:Further information:
584:, the ethyl ester of
469:
232:
33:
687:Bisulfite sequencing
479:Bisulfite is a good
191:
80:sodium metabisulfite
1252:1992PNAS...89.1827F
1170:"Glyoxal Bisulfite"
1044:Taylor, Harold M.;
821:10.1021/ic00234a026
808:Inorganic Chemistry
659:reversible reaction
523:(gold dissolved in
263:with aqueous base:
255:Acid-base reactions
204:
1046:Hauser, Charles R.
697:
556:" is used to form
529:water chlorination
472:
243:
227:
222:
206:
40:
1218:Collected Volumes
1203:Organic Syntheses
1182:Collected Volumes
1175:Organic Syntheses
1154:Collected Volumes
1147:Organic Syntheses
1126:Collected Volumes
1119:Organic Syntheses
1098:Collected Volumes
1091:Organic Syntheses
1070:Collected Volumes
1063:Organic Syntheses
1030:Collected Volumes
1023:Organic Syntheses
945:Collected Volumes
938:Organic Syntheses
815:(14): 2414–2417.
771:978-0-08-037941-8
663:addition reaction
657:group. This is a
644:Bucherer reaction
633:chromium trioxide
564:and with certain
550:organic chemistry
535:Organic synthesis
224:
1311:
1284:
1283:
1273:
1263:
1246:(5): 1827–1831.
1229:
1223:
1221:
1214:
1198:"Cycloheptanone"
1193:
1187:
1185:
1178:
1165:
1159:
1157:
1150:
1142:"Ethyl Pyruvate"
1137:
1131:
1129:
1122:
1109:
1103:
1101:
1094:
1081:
1075:
1073:
1066:
1041:
1035:
1033:
1026:
1014:Heck, Richard F.
1009:
1003:
1002:
992:
956:
950:
948:
941:
928:
922:
921:
893:
887:
886:
877:(7): 1975–1979.
866:
860:
859:
831:
825:
824:
798:
797:
796:
782:
776:
775:
760:(2nd ed.).
750:
720:5-methylcytosine
675:organic reaction
554:sodium bisulfite
544:
514:
513:
512:
498:
497:
496:
450:
449:
448:
440:
439:
429:
428:
427:
413:
412:
411:
403:
402:
379:
378:
377:
367:
366:
365:
352:
351:
350:
326:
325:
324:
296:
295:
294:
282:
281:
280:
244:
236:
234:
233:
228:
226:
225:
223:
221:
214:
207:
205:
196:
180:spectroscopy:
129:
105:
104:
103:
77:
76:
75:
65:
64:
63:
1319:
1318:
1314:
1313:
1312:
1310:
1309:
1308:
1289:
1288:
1287:
1231:
1230:
1226:
1216:
1195:
1194:
1190:
1180:
1167:
1166:
1162:
1152:
1139:
1138:
1134:
1124:
1111:
1110:
1106:
1096:
1083:
1082:
1078:
1068:
1043:
1042:
1038:
1028:
1012:Buntin, S. A.;
1011:
1010:
1006:
958:
957:
953:
943:
930:
929:
925:
895:
894:
890:
868:
867:
863:
856:
833:
832:
828:
802:
795:
792:
791:
790:
788:
784:
783:
779:
772:
752:
751:
744:
740:
689:
683:
537:
511:
508:
507:
506:
504:
502:
495:
492:
491:
490:
488:
477:
475:Redox reactions
454:
447:
444:
443:
442:
438:
435:
434:
433:
431:
426:
423:
422:
421:
419:
410:
407:
406:
405:
401:
398:
397:
396:
394:
387:
376:
373:
372:
371:
369:
364:
361:
360:
359:
357:
349:
346:
345:
344:
342:
335:
323:
320:
319:
318:
316:
312:
308:
293:
290:
289:
288:
286:
279:
276:
275:
274:
272:
270:
257:
242:
240:
189:
188:
187:
171:
169:Tautomerization
166:
159:
150:
137:
127:
125:
121:
117:
113:
102:
99:
98:
97:
95:
93:
89:
85:
74:
71:
70:
69:
67:
62:
59:
58:
57:
55:
52:hydrogensulfite
28:
17:
12:
11:
5:
1317:
1315:
1307:
1306:
1301:
1291:
1290:
1286:
1285:
1224:
1188:
1160:
1132:
1114:"Pseudoionone"
1104:
1076:
1036:
1004:
967:(134): 57639.
951:
923:
904:(2): 155–162.
888:
861:
854:
826:
800:
793:
777:
770:
741:
739:
736:
731:DNA sequencing
682:
679:
609:reducing agent
602:cycloheptanone
570:sulfonic acids
566:cyclic ketones
546:
545:
536:
533:
517:
516:
509:
500:
493:
476:
473:
457:
456:
452:
445:
436:
424:
408:
399:
386:
383:
382:
381:
374:
362:
347:
333:
321:
310:
306:
303:sulfurous acid
299:conjugate base
291:
284:
283:
277:
268:
261:sulfur dioxide
256:
253:
252:
251:
238:
220:
213:
203:
185:
170:
167:
165:
162:
157:
148:
136:
133:
132:
131:
123:
119:
115:
111:
100:
91:
87:
83:
72:
60:
15:
13:
10:
9:
6:
4:
3:
2:
1316:
1305:
1302:
1300:
1297:
1296:
1294:
1281:
1277:
1272:
1267:
1262:
1257:
1253:
1249:
1245:
1241:
1240:
1235:
1228:
1225:
1219:
1213:
1209:
1205:
1204:
1199:
1192:
1189:
1183:
1177:
1176:
1171:
1164:
1161:
1155:
1149:
1148:
1143:
1136:
1133:
1127:
1121:
1120:
1115:
1108:
1105:
1099:
1093:
1092:
1087:
1086:"β-Tetralone"
1080:
1077:
1071:
1065:
1064:
1059:
1057:
1053:
1047:
1040:
1037:
1031:
1025:
1024:
1019:
1015:
1008:
1005:
1000:
996:
991:
986:
982:
978:
974:
973:10.3791/57639
970:
966:
962:
955:
952:
946:
940:
939:
934:
927:
924:
919:
915:
911:
907:
903:
899:
892:
889:
884:
880:
876:
872:
865:
862:
857:
851:
847:
843:
839:
838:
830:
827:
822:
818:
814:
810:
809:
804:
781:
778:
773:
767:
763:
759:
755:
749:
747:
743:
737:
735:
732:
728:
723:
721:
717:
713:
708:
706:
702:
693:
688:
680:
678:
676:
673:is a related
672:
668:
664:
660:
656:
652:
649:
645:
640:
638:
634:
630:
626:
622:
618:
614:
610:
605:
603:
599:
595:
594:cyclohexanone
591:
587:
583:
579:
575:
571:
567:
563:
559:
555:
551:
543:
539:
538:
534:
532:
530:
526:
522:
486:
485:
484:
482:
474:
468:
464:
462:
417:
416:
415:
392:
391:metabisulfite
384:
356:
355:
354:
340:
336:
332:
314:
304:
300:
266:
265:
264:
262:
254:
249:
248:
211:
183:
182:
181:
179:
176:
168:
163:
161:
156:
152:
147:
142:
134:
109:
108:
107:
81:
54:) is the ion
53:
49:
45:
38:of bisulfite.
37:
32:
26:
22:
1243:
1237:
1227:
1217:
1201:
1191:
1181:
1173:
1163:
1153:
1145:
1135:
1125:
1117:
1107:
1097:
1089:
1079:
1069:
1061:
1055:
1051:
1039:
1029:
1021:
1007:
964:
954:
944:
936:
926:
901:
897:
891:
874:
870:
864:
835:
829:
812:
806:
780:
757:
724:
709:
698:
641:
625:hypochlorite
606:
586:pyruvic acid
574:benzaldehyde
547:
518:
478:
461:counter ions
458:
388:
330:
315:
285:
258:
246:
172:
154:
145:
138:
51:
43:
41:
25:Hydrosulfite
1304:Sulfur ions
701:methylation
667:double bond
578:2-tetralone
1299:Bisulfites
1293:Categories
855:3527306730
738:References
525:aqua regia
521:auric acid
271:+ OH →
160:symmetry.
981:1940-087X
219:⇀
212:−
202:↽
164:Reactions
141:tautomers
135:Structure
44:bisulfite
36:tautomers
21:Bisulfide
1048:(1973).
1016:(1990).
999:29658940
918:15017087
712:cytosine
651:hydroxyl
648:aromatic
631:esters,
613:chlorine
562:aldehyde
481:reducing
151:symmetry
1280:1542678
1248:Bibcode
990:5933314
627:salts,
617:bromine
598:diazald
590:glyoxal
558:adducts
339:sulfite
297:is the
126:O → 2
1278:
1268:
997:
987:
979:
916:
852:
768:
716:uracil
669:. The
629:osmate
621:iodine
582:citral
128:
1271:48546
799:to SO
714:into
655:amine
596:with
560:with
515:+ 2 H
503:→ 2
250:= 4.9
48:IUPAC
46:ion (
1276:PMID
1239:PNAS
1050:"α-(
995:PMID
977:ISSN
914:PMID
850:ISBN
766:ISBN
635:and
588:and
499:+ O
305:, (H
241:(OH)
122:+ H
42:The
1266:PMC
1256:doi
1208:doi
985:PMC
969:doi
906:doi
879:doi
842:doi
817:doi
789:HSO
705:DNA
552:, "
548:In
489:HSO
451:+ H
420:HSO
380:+ H
358:HSO
317:HSO
313:).
301:of
287:HSO
273:HSO
184:HSO
178:NMR
96:HSO
82:(Na
68:HSO
56:HSO
23:or
1295::
1274:.
1264:.
1254:.
1244:89
1242:.
1236:.
1215:;
1206:.
1200:.
1179:;
1172:.
1151:;
1144:.
1123:;
1116:.
1095:;
1088:.
1067:;
1060:.
1027:;
1020:.
993:.
983:.
975:.
963:.
942:;
935:.
912:.
902:60
900:.
875:33
873:.
848:.
813:25
811:.
805:.
803:H"
764:.
745:^
707:.
623:,
619:,
615:,
580:,
576:,
505:SO
487:2
463:.
430:⇌
418:2
370:SO
368:⇌
353::
343:SO
341:,
309:SO
267:SO
237:SO
149:3v
130:Na
110:Na
106:.
1282:.
1258::
1250::
1222:.
1210::
1186:.
1158:.
1130:.
1102:.
1074:.
1056:N
1054:,
1052:N
1034:.
1001:.
971::
949:.
920:.
908::
885:.
881::
858:.
844::
823:.
819::
801:3
794:3
774:.
510:4
501:2
494:3
455:O
453:2
446:5
441:O
437:2
432:S
425:3
409:5
404:O
400:2
395:S
393:(
375:3
363:3
348:3
334:a
331:K
329:p
322:3
311:3
307:2
292:3
278:3
269:2
247:K
239:2
186:3
175:O
158:s
155:C
146:C
124:2
120:5
118:O
116:2
114:S
112:2
101:3
92:5
90:O
88:2
86:S
84:2
73:3
61:3
27:.
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