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Chemical compound From Wikipedia, the free encyclopedia
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.
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Names | |
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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 | |
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.027.271 |
PubChem CID |
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Properties | |
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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DTE is a crystalline solid soluble in water and alcohols.[1][2]
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 pKa 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]
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