Dithioerythritol

Dithioerythritol
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 Y
PubChem	439352
ChemSpider	388475 Y
ChEBI	CHEBI:17456 Y
Jmol-3D images	{{#if:C([C@@H]([C@@H](CS)O)O)SSC[C@@H](O)[C@@H](O)CS|Image 1 Image 2
SMILES C([C@@H]([C@@H](CS)O)O)S SC[C@@H](O)[C@@H](O)CS
InChI InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+ Y Key: VHJLVAABSRFDPM-ZXZARUISSA-N Y InChI=1/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+ Key: VHJLVAABSRFDPM-ZXZARUISBS
Properties
Molecular formula	C4H10O2S2
Molar mass	154.25 g mol−1
Melting point	82–84 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.