334:
259:
40:
632:
31:
1034:
724:. Because of the ability to reduce disulfide bonds, DTT can be used to denature CD38 on red blood cells. DTT will also denature antigens in the Kell, Lutheran, Dombrock, Cromer, Cartwright, LW and Knops blood group systems. Conversely, the solvent exposure of different disulfide bonds can be assayed by their rate of reduction in the presence of DTT.
501:
751:
DTT is oxidized by air. So it is normally stored and handled under inert atmosphere to minimize oxidation. The rate of air-oxidation is slower at low temperatures. Oxidized DTT exhibits a strong absorbance peak at 280 nm. Since thiols are less nucleophilic than their conjugate bases,
664:
greatly lowers the efficiency of subsequent coupling reactions such as DNA immobilization on gold in biosensors. Typically DTT is mixed with a DNA solution and allowed to react, and then is removed by filtration (for the solid catalyst) or by
611:
reactions and is illustrated below. The reduction usually does not stop at the mixed-disulfide species because the second thiol of DTT has a high propensity to close the ring, forming oxidized DTT and leaving behind a reduced
966:
Cline DJ, Redding SE, Brohawn SG, Psathas JN, Schneider JP, Thorpe C (December 2004). "New water-soluble phosphines as reductants of peptide and protein disulfide bonds: reactivity and membrane permeability".
514:
696:
residues of proteins. However, even DTT cannot reduce buried (solvent-inaccessible) disulfide bonds, so reduction of disulfide bonds is sometimes carried out under
383:
771:
DTT's half-life is 40 hours at pH 6.5 and 1.4 hours at pH 8.5 and 20 °C; its half-life decreases further as temperature increases. The presence of
669:(for the liquid form). The DTT removal procedure is often called "desalting." Generally, DTT is used as a protecting agent that prevents oxidation of
768:) is an alternative reducing agent that is more stable and effective at low pH, but it is bulky and reduces cystines in folded proteins only slowly.
902:
717:
832:
348:
156:
731:. Its principal advantage is that effectively no mixed-disulfide species are populated, in contrast to other agents such as
521:
775:(ethylenediaminetetraacetic acid) to chelate divalent metal ions considerably extends the half-life of DTT in solution.
291:
764:
or DTBA), a related dithiol reducing agent, somewhat overcomes this limitation of DTT. Tris(2-carboxyethyl)phosphine (
697:
312:
607:. It has a redox potential of −0.33 V at pH 7. The reduction of a typical disulfide bond proceeds by two sequential
1002:
Stevens R, Stevens L, Price NC (1983). "The
Stabilities of Various Thiol Compounds used in Protein Purifications".
625:
1038:
720:
to further denature proteins by reducing their disulfide bonds to allow for better separation of proteins during
1059:
640:
608:
652:
DTT is used as a reducing or "deprotecting" agent for thiolated DNA. The terminal sulfur atoms of thiolated
254:
1064:
196:
743:
to different sulfur atoms; in such cases, DTT cannot cyclize since it has no such remaining free thiols.
713:
541:
705:
52:
329:
122:
572:
631:
616:. The reducing power of DTT is limited to pH values above 7, since only the negatively charged
984:
948:
898:
865:
828:
790:
661:
657:
1011:
976:
938:
930:
888:
857:
784:
761:
588:
479:
406:
216:
300:
1054:
721:
575:. The reagent is commonly used in its racemic form. Its name derives from the four-carbon
132:
333:
258:
176:
39:
943:
918:
740:
677:
666:
636:
613:
604:
600:
576:
492:
1048:
1015:
468:
458:
247:
848:
Cleland WW (April 1964). "Dithiothreitol, a New
Protective Reagent for SH Groups".
821:
280:
893:
732:
701:
670:
440:
207:
30:
988:
952:
869:
1033:
823:
Merck Index : an encyclopedia of chemicals, drugs, & biologicals
753:
693:
617:
227:
861:
236:
681:
580:
556:
267:
980:
934:
603:; once oxidized, it forms a stable six-membered ring with an internal
736:
584:
473:
125 to 130 °C (257 to 266 °F; 398 to 403 K) at 2 mmHg
187:
491:
Except where otherwise noted, data are given for materials in their
728:
630:
621:
564:
167:
155:
145:
919:"A potent, versatile disulfide-reducing agent from aspartic acid"
796:
772:
765:
709:
560:
716:). DTT is oftentimes used along with sodium dodecylsulfate in
653:
17:
357:
InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m1/s1
317:
756:, DTT becomes a less potent nucleophile as the pH falls. (2
367:
InChI=1/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m1/s1
739:
may be formed, i.e., the two sulfur atoms of DTT may form
463:
42 to 43 °C (108 to 109 °F; 315 to 316 K)
704:, or in the presence of a strong denaturant such as 6 M
887:, John Wiley & Sons, Inc., pp. 239–244, 2007,
509:
827:(13th ed.). United States: Merck & Co, Inc.
660:in solution, especially in the presence of oxygen.
820:
279:
555:. A colorless compound, it is classified as a
131:
917:Lukesh JC, Palte MJ, Raines RT (March 2012).
8:
332:
257:
215:
22:
942:
892:
299:
16:Not to be confused with banned pesticide
923:Journal of the American Chemical Society
551:
547:
814:
812:
808:
388:
353:
328:
235:
248:
692:disulfide bonds from forming between
676:DTT is frequently used to reduce the
628:of the thiol groups is 9.2 and 10.1.
360:Key: VHJLVAABSRFDPM-QWWZWVQMSA-N
195:
175:
7:
620:form -S is reactive (the protonated
370:Key: VHJLVAABSRFDPM-QWWZWVQMBU
270:
65:)-1,4-Bis(sulfanyl)butane-2,3-diol
14:
1032:
760:)-2-Amino-1,4-dimercaptobutane (
684:and, more generally, to prevent
499:
418:
38:
29:
495:(at 25 °C , 100 kPa).
82:)-1,4-Dimercaptobutane-2,3-diol
430:
424:
412:
100:-1,4-Dimercapto-2,3-butanediol
91:-1,4-Dimercaptobutane-2,3-diol
1:
1016:10.1016/0307-4412(83)90048-1
894:10.1002/9780470238165.indsp1
735:. In very rare cases, a DTT
727:DTT can also be used as an
445:154.253 g/mol
1081:
639:by DTT via two sequential
15:
883:"NLM PubChem CID Index",
489:
399:
379:
344:
115:
71:
51:
46:
37:
28:
656:have a tendency to form
641:thiol-disulfide exchange
609:thiol-disulfide exchange
819:O'Neil MJ, ed. (2001).
635:Reduction of a typical
644:
624:form -SH is not); the
567:reagent also known as
1004:Biochemical Education
714:sodium dodecylsulfate
698:denaturing conditions
634:
587:('sister') compound,
542:organosulfur compound
1041:at Wikimedia Commons
706:guanidinium chloride
53:Preferred IUPAC name
862:10.1021/bi00892a002
480:Solubility in water
25:
885:Vitamin D Handbook
645:
573:W. Wallace Cleland
522:Infobox references
23:
1037:Media related to
981:10.1021/bi048329a
975:(48): 15195–203.
935:10.1021/ja211931f
904:978-0-470-23816-5
791:2-Mercaptoethanol
569:Cleland's reagent
544:with the formula
530:Chemical compound
528:
527:
313:CompTox Dashboard
157:Interactive image
108:Cleland's reagent
105:
95:
86:
1072:
1036:
1020:
1019:
999:
993:
992:
963:
957:
956:
946:
914:
908:
907:
896:
880:
874:
873:
845:
839:
838:
826:
816:
785:Dithiobutylamine
762:dithiobutylamine
589:dithioerythritol
554:
512:
506:
503:
502:
432:
426:
420:
414:
407:Chemical formula
337:
336:
321:
319:
303:
283:
272:
261:
250:
239:
219:
199:
179:
159:
135:
103:
93:
84:
42:
33:
26:
1080:
1079:
1075:
1074:
1073:
1071:
1070:
1069:
1060:Reducing agents
1045:
1044:
1029:
1024:
1023:
1001:
1000:
996:
965:
964:
960:
916:
915:
911:
905:
882:
881:
877:
847:
846:
842:
835:
818:
817:
810:
805:
781:
749:
741:disulfide bonds
729:oxidizing agent
722:electrophoresis
700:(e.g., at high
678:disulfide bonds
650:
597:
553:
549:
545:
531:
524:
519:
518:
517: ?)
508:
504:
500:
496:
482:
435:
429:
423:
417:
409:
395:
392:
387:
386:
375:
372:
371:
368:
362:
361:
358:
352:
351:
340:
322:
315:
306:
286:
273:
242:
222:
202:
182:
162:
149:
138:
125:
111:
109:
107:
101:
92:
83:
67:
66:
24:Dithiothreitol
21:
12:
11:
5:
1078:
1076:
1068:
1067:
1062:
1057:
1047:
1046:
1043:
1042:
1039:Dithiothreitol
1028:
1027:External links
1025:
1022:
1021:
994:
958:
909:
903:
875:
840:
833:
807:
806:
804:
801:
800:
799:
794:
788:
780:
777:
748:
745:
690:intermolecular
686:intramolecular
667:chromatography
649:
646:
637:disulfide bond
614:disulfide bond
605:disulfide bond
601:reducing agent
596:
595:Reducing agent
593:
534:Dithiothreitol
529:
526:
525:
520:
498:
497:
493:standard state
490:
487:
486:
483:
478:
475:
474:
471:
465:
464:
461:
455:
454:
451:
447:
446:
443:
437:
436:
433:
427:
421:
415:
410:
405:
402:
401:
397:
396:
394:
393:
390:
382:
381:
380:
377:
376:
374:
373:
369:
366:
365:
363:
359:
356:
355:
347:
346:
345:
342:
341:
339:
338:
325:
323:
311:
308:
307:
305:
304:
296:
294:
288:
287:
285:
284:
276:
274:
266:
263:
262:
252:
244:
243:
241:
240:
232:
230:
224:
223:
221:
220:
212:
210:
204:
203:
201:
200:
192:
190:
184:
183:
181:
180:
172:
170:
164:
163:
161:
160:
152:
150:
143:
140:
139:
137:
136:
128:
126:
121:
118:
117:
113:
112:
73:
69:
68:
56:
55:
49:
48:
44:
43:
35:
34:
13:
10:
9:
6:
4:
3:
2:
1077:
1066:
1065:Vicinal diols
1063:
1061:
1058:
1056:
1053:
1052:
1050:
1040:
1035:
1031:
1030:
1026:
1017:
1013:
1009:
1005:
998:
995:
990:
986:
982:
978:
974:
970:
962:
959:
954:
950:
945:
940:
936:
932:
929:(9): 4057–9.
928:
924:
920:
913:
910:
906:
900:
895:
890:
886:
879:
876:
871:
867:
863:
859:
855:
851:
844:
841:
836:
834:0-911910-13-1
830:
825:
824:
815:
813:
809:
802:
798:
795:
792:
789:
786:
783:
782:
778:
776:
774:
769:
767:
763:
759:
755:
746:
744:
742:
738:
734:
730:
725:
723:
719:
715:
711:
707:
703:
699:
695:
691:
687:
683:
679:
674:
672:
668:
663:
659:
655:
647:
642:
638:
633:
629:
627:
623:
619:
615:
610:
606:
602:
594:
592:
590:
586:
583:. DTT has an
582:
578:
574:
570:
566:
562:
558:
543:
539:
535:
523:
516:
511:
494:
488:
484:
481:
477:
476:
472:
470:
469:Boiling point
467:
466:
462:
460:
459:Melting point
457:
456:
452:
449:
448:
444:
442:
439:
438:
411:
408:
404:
403:
398:
389:
385:
378:
364:
354:
350:
343:
335:
331:
330:DTXSID5041017
327:
326:
324:
314:
310:
309:
302:
298:
297:
295:
293:
290:
289:
282:
278:
277:
275:
269:
265:
264:
260:
256:
253:
251:
249:ECHA InfoCard
246:
245:
238:
234:
233:
231:
229:
226:
225:
218:
214:
213:
211:
209:
206:
205:
198:
197:ChEMBL1232392
194:
193:
191:
189:
186:
185:
178:
174:
173:
171:
169:
166:
165:
158:
154:
153:
151:
147:
142:
141:
134:
130:
129:
127:
124:
120:
119:
114:
99:
90:
81:
77:
70:
64:
60:
54:
50:
45:
41:
36:
32:
27:
19:
1007:
1003:
997:
972:
969:Biochemistry
968:
961:
926:
922:
912:
884:
878:
856:(4): 480–2.
853:
850:Biochemistry
849:
843:
822:
770:
757:
750:
726:
702:temperatures
689:
685:
675:
671:thiol groups
662:Dimerization
651:
648:Applications
598:
568:
537:
533:
532:
453:White solid
391:C(((CS)O)O)S
116:Identifiers
97:
88:
79:
75:
72:Other names
62:
58:
733:glutathione
450:Appearance
400:Properties
255:100.020.427
177:CHEBI:42170
110:Reductacryl
102:1,4-Dithio-
1049:Categories
803:References
747:Properties
643:reactions.
441:Molar mass
301:T8ID5YZU6Y
208:ChemSpider
144:3D model (
123:CAS Number
1010:(2): 70.
754:thiolates
599:DTT is a
563:. DTT is
546:(CH(OH)CH
133:3483-12-3
106:-threitol
989:15568811
953:22353145
870:14192894
779:See also
718:SDS-PAGE
712:, or 1%
694:cysteine
682:proteins
618:thiolate
585:epimeric
571:, after
540:) is an
485:Soluble
228:DrugBank
944:3353773
591:(DTE).
581:threose
557:dithiol
515:what is
513: (
268:PubChem
237:DB04447
1055:Thiols
987:
951:
941:
901:
868:
831:
787:(DTBA)
737:adduct
708:, 8 M
658:dimers
559:and a
510:verify
507:
384:SMILES
281:446094
217:393541
188:ChEMBL
47:Names
793:(BME)
622:thiol
577:sugar
565:redox
349:InChI
168:ChEBI
146:JSmol
98:threo
89:threo
985:PMID
949:PMID
899:ISBN
866:PMID
829:ISBN
797:TCEP
773:EDTA
766:TCEP
710:urea
688:and
561:diol
292:UNII
1012:doi
977:doi
939:PMC
931:doi
927:134
889:doi
858:doi
680:of
654:DNA
626:pKa
550:SH)
538:DTT
318:EPA
271:CID
18:DDT
1051::
1008:11
1006:.
983:.
973:43
971:.
947:.
937:.
925:.
921:.
897:,
864:.
852:.
811:^
673:.
579:,
422:10
78:,3
74:(2
61:,3
57:(2
1018:.
1014::
991:.
979::
955:.
933::
891::
872:.
860::
854:3
837:.
758:S
552:2
548:2
536:(
505:N
434:2
431:S
428:2
425:O
419:H
416:4
413:C
320:)
316:(
148:)
104:D
96:-
94:D
87:-
85:D
80:S
76:S
63:S
59:S
20:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
