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	6892-68-8^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:17456^Y
ChemSpider	388475^Y
ECHA InfoCard	100.027.271
PubChem CID	439352
UNII	R4SVL81GQI^Y
CompTox Dashboard (EPA)	DTXSID40884341
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
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). Y verify (what is ^YN ?) Infobox references

Chemical compound

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

Chemical properties

DTE is a crystalline solid soluble in water and alcohols.^[1]^[2]

Applications

Like DTT, DTE makes an excellent reducing agent, which can be used for reduction of disulfide bonds. The reduction potential of DTE is the same as for DTT, about –0.331 mV.^[2] The pK_a values of the thiol groups of DTE are 9.0 and 9.9, which is higher than the corresponding values for DTT (9.3 and 9.5).^[2] Since reduction of disulfide bonds requires thiolate (ionized thiol), DTE is less efficient at lower pH compared to DTT.^[2]

Reduction with DTE is slower than with 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.^[3]

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.
^ ^a ^b ^c ^d Jocelyn, Peter C. (1987). "Chemical reduction of disulfides". Sulfur and Sulfur Amino Acids. Methods in Enzymology. Vol. 143. Academic Press. pp. 246–256. doi:10.1016/0076-6879(87)43048-6. ISBN 9780121820435. PMID 3657541.
^ Loechler, Edward L.; Hollocher, Thomas C. (November 1980). "Reduction of flavins by thiols. 1. Reaction mechanism from the kinetics of the attack and breakdown steps". Journal of the American Chemical Society. 102 (24): 7312–7321. doi:10.1021/ja00544a027. ISSN 0002-7863.