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Dithiothreitol (DTT, Cleland's reagent)

CAS No.
3483-12-3

Application: Reducing agent

Synonyms

(2S,3S)-1,4-Bis-sulfanylbutane-2,3-diol, Threo-1,4-dimercaptobutane-2,3-diol, DL-Threo-1,4-dimercapto-2,3-butanediol, 1,4-Dithio-DL-threitol, ±-Threo-1,4-dimercapto2,3-butanediol Cleland's reagent, Reductacryl

TECHNICAL PROFILE

Technical name: Dithiothreitol (DTT)

CAS No: 3483-12-3

Empirical formula: C4H10O2S2

Molecular weight: 154.253 g/mol

 

GENERAL DESCRIPTION

Dithiothreitol (DTT) is a well-known small-molecule redox reagent, widely used for the reduction of disulfide bridges in proteins. It is also known as Cleland's reagent and it has various applications in biotechnology, biology, and biochemistry.

It is an epimeric compound of dithioerythritol (DTE).

REDUCING PROPERTIES

Dithiothreitol is a particularly strong reducing agent with a redox potential of -0.33 V at pH 7. Once in its oxidized state, it forms a stable six-membered ring structure with an internal disulfide bond.

The reduction of a typical disulfide bond is followed by two sequential thiol-disulfide exchange reactions.

SOLUBILITY

DTT is highly soluble in water (clear solution, OD<0.05 at 0.02M), forming a clear, colourless solution. DTT is also soluble in ethanol, chloroform, acetone, ethylate, and ether. DTT solutions should be prepared fresh daily.

APPLICATIONS

DTT is suitable for use in molecular biology or protein biochemistry applications to reduce disulfide bridges, protect biomolecules, as well as in sample preparation, and in reconstructing proteins before electrophoresis analysis.

It is frequently used to reduce the dissulfide bonds of proteins and peptides.

As an antioxidant, DTT is applied as a protective agent against ionizing radiations in living cells [1], while it is used to produce biofuel, and lead apoptosis.

Dithiothreitol is used as an oxidizing agent to effectively prevent the population of mixed-disulfide species. In some instances, it may form an adduct, i.e. the two sulfur atoms of DTT may form disulfide bonds to different sulfur atoms; in such cases, DTT cannot cyclize, since there are no free thiols remaining.

References

  1. Bick, Y., Jackson, W. 1968. Chemical Protection against X-irradiation by a New Reducing Agent 1,4-Dithiothreitol in Marsupial Leucocytes in Culture. Nature 217, 479–480. DOI: https://doi.org/10.1038/217479a0
Chemical structure for Dithiothreitol (DTT, Cleland's reagent)

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