Dithioerythritol

Chemical properties

DTE is a crystalline solid soluble in water and alcohols.

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. 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). Since reduction of disulfide bonds requires thiolate (ionized thiol), DTE is less efficient at lower pH compared to DTT.

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.

References

References

1. Cleland, W.W.. (April 1964). "Dithiothreitol, A New Protective Reagent for SH Groups". Biochemistry.
2. (1987). "Sulfur and Sulfur Amino Acids". Academic Press.
3. (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.