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Dithiothreitol

Dithiothreitol

Synopsis, Chemistry

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Also known as: Dithiothreitol, Dl-1,4-dithiothreitol, 3483-12-3, Dl-dithiothreitol, 1,4-dithiothreitol, D-dithiothreitol

Molecular Formula

C₄H₁₀O₂S₂

Molecular Weight

154.3 g/mol

InChI Key

VHJLVAABSRFDPM-QWWZWVQMSA-N

A reagent commonly used in biochemical studies as a protective agent to prevent the oxidation of SH (thiol) groups and for reducing disulphides to dithiols.

1 2D Structure

Dithiothreitol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S)-1,4-bis(sulfanyl)butane-2,3-diol

2.1.2 InChI

InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m1/s1

2.1.3 InChI Key

VHJLVAABSRFDPM-QWWZWVQMSA-N

2.1.4 Canonical SMILES

C(C(C(CS)O)O)S

2.1.5 Isomeric SMILES

C([C@H]([C@@H](CS)O)O)S

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Cleland Reagent

2. Cleland's Reagent

3. Clelands Reagent

4. Dithiothreitol

5. Reagent, Cleland

6. Reagent, Cleland's

7. Sputolysin

2.2.2 Depositor-Supplied Synonyms

1. Dithiothreitol

2. Dl-1,4-dithiothreitol

3. 3483-12-3

4. Dl-dithiothreitol

5. 1,4-dithiothreitol

6. D-dithiothreitol

7. D-1,4-dithiothreitol

8. 27565-41-9

9. D-dtt

10. (2s,3s)-1,4-bis(sulfanyl)butane-2,3-diol

11. (2s,3s)-1,4-disulfanylbutane-2,3-diol

12. Dtt

13. Mfcd00004877

14. D-threo-1,4-dimercapto-2,3-butanediol

15. Threo-1,4-dimercapto-2,3-butanediol

16. Chebi:42170

17. Cis-2,3-dihydroxy-1,4-butanedithiol

18. 35454-97-8

19. Sputolysin

20. Rac-dithiothreitol

21. Dtv

22. 1,4-dithiothreithol

23. Dithio Threitol

24. Wr 34678

25. Reagents, Cleland's

26. 2,3-butanediol, 1,4-dimercapto-, (r*,r*)-

27. (+/-)-dithiothreitol

28. Dl-dithiothreitol, 99%

29. Dl-dithiothreitol, Powder

30. Dtt (threitol Derivative)

31. Dtt, 1,4-dithiothreitol

32. D,l-dithiothreitol (dtt)

33. Schembl10601

34. Threitol, 1,4-dithio-, L-

35. Chembl1232392

36. Dl-dithiothreitol, >=99.0%

37. Dtxsid5041017

38. Dithiothreitol, Biochemical Grade

39. 1,4-dimercapto-butane-2,3-diol

40. Zinc3852211

41. Einecs 240-263-0

42. Ethyl4-nitro-l-phenylalanine

43. Akos005259570

44. Akos015855399

45. Ccg-207964

46. Db02184

47. Dl-dithiothreitol, >=99.0% (rt)

48. Threitol, 1,4-dithio- (7ci,8ci)

49. Brn 2036371

50. Threo-2,3-dihydroxy-1,4-butanedithiol

51. Dl-1,4-dimercapto-2,3-dihydroxybutane

52. Dtt, Dithiothreitol (cleland's Reagenz)

53. (+/-)-1,4-dimercapto-2,3-butanediol

54. As-57473

55. Bp-22785

56. Dl-dithiothreitol Solution, 1 M In H2o

57. B7294

58. D97824

59. Dl-dithiothreitol, Bioultra, >=99.0% (rt)

60. Dl-dithiothreitol, For Electrophoresis, >=99%

61. M02712

62. M02716

63. (r-(r*,r*))-1,4-dimercaptobutane-2,3-diol

64. Dl-dithiothreitol, Saj Special Grade, >=98.0%

65. Dl-dithiothreitol, Vetec(tm) Reagent Grade, 98%

66. Q414783

67. (+/-) Dithiothreitol Molecular Biology Grade >99%

68. 2,3-butanediol, 1,4-dimercapto-, L-threo-

69. Dl-dithiothreitol, Bioxtra, >=99.0% (titration)

70. 2,3-butanediol, 1,4-dimercapto-, (r-(r*,r*))-

71. 2,3-butanediol, 1,4-dimercapto-, (2r,3r)-rel- (9ci)

72. Dl-dithiothreitol, >=98% (hplc), >=99.0% (titration)

73. Dl-dithiothreitol; Cleland Inverted Exclamation Mark S Reagent

74. Dl-dithiothreitol, Bioultra, For Molecular Biology, >=99.5% (rt)

75. Dl-dithiothreitol Solution, Bioultra, For Molecular Biology, ~1 M In H2o

76. Dl-dithiothreitol, For Molecular Biology, >=98% (hplc), >=99% (titration)

2.3 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₄H₁₀O₂S₂
Molecular Weight	154.3 g/mol
XLogP3	-0.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	154.01222190 g/mol
Monoisotopic Mass	154.01222190 g/mol
Topological Polar Surface Area	42.5 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	52
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

Two male patients with late stage (uremic) infantile nephropathic cystinosis (INC) were treated by mouth with the reducing agent dithiothreitol (DTT), at doses not exceeding 25 mg/kg body weight three times per day. Three sequential periods of observation were obtained in both patients: on thiol (8.5 months); off thiol (8-9 months); on thiol again (7 months or longer)... Whereas chemical methods are not reliable for detecting and measuring DTT in biologic fluids, preliminary evidence indicates that a silylated derivative of oxidized DTT can be detected in the urine of patients receiving DTT by mouth. This finding suggests that the thiol is absorbed and excreted.

PMID:840501 Depape-Brigger D et al; Pediatr Res 11 (2): 124-31 (1977)

4.2 Metabolism/Metabolites

PMID:840501 Depape-Brigger D et al; Pediatr Res 11 (2): 124-31 (1977)