Dithioerythritol

Dithioerythritol
Names
Preferred IUPAC name
(2R,3S)-1,4-Bis(sulfanyl)butane-2,3-diol
Other names
(2R,3S)-1,4-Dimercaptobutane-2,3-diol (no longer recommended)
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.027.271
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PubChem CID
UNII
InChI
  • InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+ checkY
    Key: VHJLVAABSRFDPM-ZXZARUISSA-N checkY
  • InChI=1/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+
    Key: VHJLVAABSRFDPM-ZXZARUISBS
SMILES
  • C([C@@H]([C@@H](CS)O)O)S
  • SC[C@@H](O)[C@@H](O)CS
Properties
Chemical formula
 C4H10O2S2
Molar mass 154.253 g/mol
Melting point 82 to 84 °C (180 to 183 °F; 355 to 357 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox 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. This is presumably because the orientation of the OH groups in its cyclic disulfide-bonded form (oxidized form) is less stable due to greater steric repulsion than their orientation in the disulfide-bonded form of DTT. In the disulfide-bonded form of DTT, these hydroxyl groups are trans to each other, whereas they are cis to each other in DTE.

The oxidized forms of dithioerythritol (DTE, left) and dithiothreitol (DTT, right).

References

  • Cleland, W.W. (April 1964). "Dithiothreitol, A New Protective Reagent for SH Groups". Biochemistry. 3 (4): 480–2. doi:10.1021/bi00892a002. PMID 14192894.
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