Dithioerythritol

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Dithioerythritol
IUPAC name (2S,3R)-1,4-Bis-sulfanylbutane-2,3-diol
Other names 2,3-Dihydroxybutane-1,4-dithiol
Erythro-2,3-dihydroxy-1,4-butanedithiol
Erythro-1,4-dimercapto-2,3-butanediol
Cleland's reagent (also used for DTT)
Identifiers
CAS number [6892-68-8]
PubChem 439352
SMILES C([C@@H]([C@@H](CS)O)O)S
Properties
Molecular formula C4H10O2S2
Molar mass 154.253 g/mol
Melting point

82-84 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dithioerythritol (DTE) is a sulfur containing sugar derived from the corresponding 4-carbon monosaccharide erythrose. It is an epimer of dithiothreitol (DTT). The molecular formula for DTE is C4H10O2S2.

Like DTT, DTE makes an excellent reducing agent, although its standard reduction potential is not quite as negative, i.e., DTE is slightly less effective at reducing than DTT, presumably because steric repulsion of its OH groups makes the cyclic disulfide-bonded form of DTE less favorable. In DTT, these hydroxyl groups are on opposite sides of the ring, whereas they are on the same side of the ring (and, hence, closer) in DTE.

Oxidized disulfide form of dithioerythritol
Oxidized disulfide form of dithioerythritol


[edit] References

  • Cleland WW. (1964) "Dithiothreitol, A New Protective Reagent for SH Groups", Biochemistry, 3, 480-482.
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