Dithioerythritol

Dithioerythritol

Names
IUPAC name (2S,3R)-1,4-Bis-sulfanylbutane-2,3-diol
Other names (2R,3S)-1,4-dimercaptobutane-2,3-diol 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
ChEBI	CHEBI:17456
ChemSpider	388475
Jmol interactive 3D	Image Image
PubChem	439352
InChI InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+ Key: VHJLVAABSRFDPM-ZXZARUISSA-N 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, presumably because steric repulsion of its OH groups makes the cyclic disulfide-bonded form of DTE less stable compared to that of DTT. In 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) 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.