Dithiothreitol



Dithiothreitol[1]
IUPAC name (2S,3S)-1,4-Bis-sulfanylbutane-2,3-diol
Other names Threo-1,4-dimercaptobutane-2,3-diol
DL-Threo-1,4-dimercapto-2,3-butanediol
1,4-Dithio-DL-threitol
±-Threo-1,4-dimercapto-2,3-butanediol
Cleland's reagent
Reductacryl
Identifiers
CAS number 3483-12-3
PubChem 446094
SMILES SC[C@@H](O)[C@H](O)CS
Properties
Molecular formula C4H10O2S2
Molar mass 154.253 g/mol
Appearance White solid
Melting point

42-43 °C

Boiling point

125-130 °C at 2 mmHg

Solubility in water Soluble
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Dithiothreitol (DTT) is the common name for a small-molecule epimeric ('sister') compound, dithioerythritol (DTE).

Reducing agent

DTT is an unusually strong pKa of thiol groups is typically ~8.3.

 

Applications

A common use of DTT is as a reducing or "deprotecting" agent for thiolated DNA. The terminal sulfur atoms of thiolated chromatography (for the liquid form). The DTT removal procedure is often called "desalting."

DTT is frequently used to reduce the urea, or 1% Sodium dodecylsulfate). Conversely, the solvent exposure of different disulfide bonds can be assayed by their rate of reduction in the presence of DTT.

DTT can also be used as an disulfide bonds to different sulfur atoms; in such cases, DTT cannot cyclize since it has no remaining free thiols.

Properties

Due to air oxidation, DTT is a relatively unstable compound whose useful life can be extended by refrigeration and handling in an inert atmosphere. Since protonated sulfurs have lowered nucleophilicities, DTT becomes less potent as the pH lowers. Tris(2-carboxyethyl)phosphine HCl (TCEP hydrochloride) is an alternative which is more stable and works even at low pH.

References

  1. ^ Merck Index, 11th Edition, 3382.
  • Cleland WW. (1964) "Dithiothreitol, A New Protective Reagent for SH Groups", Biochemistry, 3, 480-482.
  • Ruegg UT and Rudinger J. (1977) "Cleavage of disulfide bonds in proteins", Methods Enzymol., 47, 111.
 
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