24:
251:
160:
33:
591:, are similar to dansyl chloride in absorption and fluorescence characteristics. But even for dansyl chloride, there are a variety of extinction coefficient values that have been reported. Some of the values are used to estimate the extent of success in attempts to conjugate the dye to a protein. Other values may be used to determine a precise concentration of a stock solution. See the table below for specific values and their uses.
408:
494:
586:
The extinction coefficient of dansyl derivatives are important for measuring their concentration in solution. Dansyl chloride is one of the simplest sulfonamide derivatives, so it commonly serves as a starting reagent for the production of other derivatives. Exotic derivatives may have very
598:
that appears between 310 nm and 350 nm. The peak is broad, so the measurement is not very sensitive to wavelength miscalibration of the spectrophotometer, and error due to miscalibration can be avoided by taking the value at the maximum instead of strictly using 330 nm.
1003:
388:
815:"Microanalysis of proteins and peptides. I. Enhancement of the fluorescence intensity of dansyl amino acids and dansyl proteins in aqueous media and its application to assay of amino acids and proteins"
456:
507:
448:
300:
560:
In addition, these protein-DNSC conjugates are sensitive to their immediate environment. This, in combination with their ability to accept energy (as in
452:
1064:
702:
561:
541:
sulfonamide adducts. It can also be made to react with secondary amines. Dansyl chloride is widely used to modify amino acids; specifically,
789:
748:
265:
23:
1079:
97:
444:
514:
430:
208:
229:
1069:
1004:"Molecular Probes Handbook: Coumarins, Pyrenes and Other Ultraviolet Light–Excitable Fluorophores (Section 1.7)"
1059:
572:
854:
Boyle, RE (1966). "The
Reaction of Dimethyl Sulfoxide and 5-Dimethylaminonaphthalene-1-sulfonyl Chloride".
407:
155:
678:
1074:
881:
Hartley, BS; V Massey (1956). "The active center of chymotrypsin: 1. Labelling with a fluorescent dye".
416:
400:
710:
460:
45:
622:
Use for DNSC-protein conjugates; Used to determine degree of labeling in chymotrypsin and ovalbumin
246:
63:
1026:
580:
576:
542:
1024:
Arthur Mendel (1970). "Improved preparation of 5-dimethylamino-1-naphthalenesulfonyl chloride".
436:
985:
933:
898:
836:
795:
785:
754:
744:
1035:
975:
967:
925:
890:
863:
826:
777:
736:
323:
568:, allows this labeling technique to be used in investigating protein folding and dynamics.
464:
217:
137:
32:
73:
468:
250:
159:
117:
980:
955:
677:
This compound may be prepared by reacting the corresponding sulfonic acid with excess
485:
422:
1053:
929:
894:
706:
373:
148:
476:
588:
554:
538:
440:
274:
InChI=1S/C12H12ClNO2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3
181:
284:
InChI=1/C12H12ClNO2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3
781:
740:
731:
Walker JM (1994). "The Dansyl Method for
Identifying N-Terminal Amino Acids".
565:
546:
360:
128:
537:
in both aliphatic and aromatic amines to produce stable blue- or blue-green–
989:
902:
937:
840:
799:
758:
594:
For all of the studies below, the absorption value is always taken at the
1039:
867:
831:
814:
168:
971:
772:
Walker JM (1994). "The Dansyl-Edman Method for
Peptide Sequencing".
484:
Except where otherwise noted, data are given for materials in their
666:
Conditions are not given; no reference to the source of this value
583:, which should never be used to prepare solutions of the reagent.
534:
192:
108:
96:
86:
472:
234:
633:
In bicarbonate buffer; maximum is shifted to ~315 nm
587:
different extinction coefficients, but others, such as
502:
776:. Methods Mol. Biol. Vol. 32. pp. 329–34.
735:. Methods Mol. Biol. Vol. 32. pp. 321–8.
601:
531:5-(dimethylamino)naphthalene-1-sulfonyl chloride
180:
50:5-(Dimethylamino)naphthalene-1-sulfonyl chloride
72:
956:"Polarized fluorescence of Protein Conjugates"
549:analysis. Dansyl chloride may also be denoted
8:
916:Chen, RF (1968). "Dansyl labeled proteins".
949:
947:
249:
158:
136:
15:
979:
830:
216:
655:In 60% ethanol; Measured at 329 nm
813:Kinoshita T, Iinuma F, Tsuji A (1974).
694:
305:
270:
245:
644:In water; peak shifted to 312 nm
562:fluorescence resonance energy transfer
149:
378:70 °C (158 °F; 343 K)
277:Key: XPDXVDYUQZHFPV-UHFFFAOYSA-N
116:
7:
774:Basic Protein and Peptide Protocols
733:Basic Protein and Peptide Protocols
553:. Likewise, a similar derivative,
287:Key: XPDXVDYUQZHFPV-UHFFFAOYAI
171:
575:adducts can be enhanced by adding
14:
579:. Dansyl chloride is unstable in
856:The Journal of Organic Chemistry
492:
406:
344:
341:
335:
31:
22:
488:(at 25 °C , 100 kPa).
1065:Reagents for organic chemistry
533:is a reagent that reacts with
353:
347:
329:
308:ClS(=O)(=O)c1cccc2c1cccc2N(C)C
1:
883:Biochimica et Biophysica Acta
930:10.1016/0003-2697(68)90116-4
895:10.1016/0006-3002(56)90093-2
662:
651:
640:
629:
618:
1096:
571:The fluorescence of these
782:10.1385/0-89603-268-X:329
741:10.1385/0-89603-268-X:321
482:
387:
382:
316:
296:
261:
56:
44:
39:
30:
21:
608:Extinction Coefficient
431:Precautionary statements
1080:Dimethylamino compounds
918:Analytical Biochemistry
685:) at room temperature.
679:phosphorus oxychloride
564:) from the amino acid
535:primary amino groups
46:Preferred IUPAC name
1040:10.1021/je60045a010
960:Biochemical Journal
868:10.1021/jo01349a529
832:10.1248/cpb.22.2413
368: g·mol
18:
1027:J. Chem. Eng. Data
581:dimethyl sulfoxide
577:alpha-cyclodextrin
557:is known as DNSA.
543:protein sequencing
515:Infobox references
16:
972:10.1042/bj0510145
954:Weber, G (1952).
862:(11): 3880–3882.
819:Chem. Pharm. Bull
670:
669:
523:Chemical compound
521:
520:
417:Hazard statements
230:CompTox Dashboard
98:Interactive image
1087:
1070:Sulfonyl halides
1044:
1043:
1021:
1015:
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994:
993:
983:
951:
942:
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913:
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851:
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844:
834:
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721:
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718:
709:. Archived from
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324:Chemical formula
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140:
120:
100:
76:
35:
26:
19:
17:Dansyl chloride
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1086:
1085:
1084:
1050:
1049:
1048:
1047:
1023:
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1001:
997:
953:
952:
945:
915:
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910:
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853:
852:
848:
825:(10): 2413–20.
812:
811:
807:
792:
771:
770:
766:
751:
730:
729:
725:
716:
714:
701:
700:
696:
691:
684:
675:
527:Dansyl chloride
524:
517:
512:
511:
510: ?)
501:
497:
493:
489:
433:
419:
403:
365:
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103:
90:
79:
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51:
12:
11:
5:
1093:
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1083:
1082:
1077:
1072:
1067:
1062:
1060:Chemical tests
1052:
1051:
1046:
1045:
1034:(2): 340–341.
1016:
995:
966:(2): 145–155.
943:
924:(1): 412–416.
908:
873:
846:
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790:
764:
749:
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609:
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522:
519:
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491:
490:
486:standard state
483:
480:
479:
457:P305+P351+P338
449:P303+P361+P353
434:
429:
426:
425:
420:
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412:
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28:
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2:
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828:
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801:
797:
793:
791:0-89603-268-X
787:
783:
779:
775:
768:
765:
760:
756:
752:
750:0-89603-268-X
746:
742:
738:
734:
727:
724:
713:on 2007-12-27
712:
708:
707:Sigma-Aldrich
704:
698:
695:
688:
686:
680:
672:
665:
659:
658:
654:
648:
647:
643:
637:
636:
632:
626:
625:
621:
616:DNSC-protein
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614:
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590:
584:
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569:
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398:
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386:
381:
377:
375:
374:Melting point
372:
371:
364:
362:
359:
358:
328:
325:
321:
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315:
306:
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295:
281:
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247:DTXSID2060543
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150:ECHA InfoCard
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65:
61:
60:
55:
47:
43:
38:
34:
29:
25:
20:
1075:Naphthalenes
1031:
1025:
1019:
1007:. Retrieved
998:
963:
959:
921:
917:
911:
889:(1): 58–70.
886:
882:
876:
859:
855:
849:
822:
818:
808:
773:
767:
732:
726:
715:. Retrieved
711:the original
697:
676:
595:
593:
589:dansyl amide
585:
570:
559:
555:dansyl amide
550:
530:
526:
525:
389:
193:RTECS number
57:Identifiers
673:Preparation
573:sulfonamide
539:fluorescent
317:Properties
156:100.009.175
118:CHEBI:51907
1054:Categories
717:2007-12-02
689:References
566:tryptophan
547:amino acid
401:Pictograms
361:Molar mass
218:QMU9166TJ4
129:ChemSpider
85:3D model (
64:CAS Number
453:P304+P340
392:labelling
200:QK3688000
990:14944566
903:13363860
605:Species
383:Hazards
74:605-65-2
1009:12 June
981:1197814
938:5704757
841:4468087
800:7951733
759:7951732
596:maximum
508:what is
506: (
169:PubChem
988:
978:
936:
901:
839:
798:
788:
757:
747:
703:"MSDS"
611:Notes
503:verify
500:
366:269.74
301:SMILES
40:Names
681:(POCl
663:4000
660:DNSC
652:4050
649:DNSA
641:4550
638:DNSC
630:4350
627:DNSC
619:3300
266:InChI
182:11801
138:11308
109:ChEBI
87:JSmol
1011:2009
986:PMID
934:PMID
899:PMID
837:PMID
796:PMID
786:ISBN
755:PMID
745:ISBN
551:DNSC
545:and
477:P501
473:P405
469:P363
465:P321
461:P310
445:P280
441:P264
437:P260
423:H314
209:UNII
1036:doi
976:PMC
968:doi
926:doi
891:doi
864:doi
827:doi
778:doi
737:doi
529:or
390:GHS
235:EPA
172:CID
1056::
1032:15
1030:.
984:.
974:.
964:51
962:.
958:.
946:^
932:.
922:25
920:.
897:.
887:21
885:.
860:31
858:.
835:.
823:22
821:.
817:.
794:.
784:.
753:.
743:.
705:.
475:,
471:,
467:,
463:,
459:,
455:,
451:,
447:,
443:,
439:,
394::
342:Cl
339:12
333:12
1042:.
1038::
1013:.
992:.
970::
940:.
928::
905:.
893::
870:.
866::
843:.
829::
802:.
780::
761:.
739::
720:.
683:3
498:Y
354:S
351:2
348:O
345:N
336:H
330:C
237:)
233:(
89:)
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