DL-Dithiothreitol(3483-12-3)

Brief introduction: dithiothreitol is a common reductant, also called dithiothreitol (DTT), which has strong reducibility. Its reducibility is largely due to the conformational stability of its oxidized six-membered ring (containing disulfide bond). The reducing force is affected by the pH value, and can only play a reducing role when the pH value is greater than 7. This is because only the proton-removed mercaptan anion (- S –) has reactivity, while mercaptan (- SH) does not; The pKa of sulfhydryl group is generally~8.3.

Application: dithiothreitol (DTT) is a small molecular organic reducing agent with chemical formula of C4H10O2S2. It is mainly used in the field of biotechnology as a protein cracking reagent. At present, the most widely used method for the synthesis of dithiothreitol is to take threitol as raw material, first oxidize it with potassium permanganate, then obtain the thiointermediate under the action of thioacetic acid, and finally hydrolyze the thiointermediate to obtain dithiothreitol.

Chemical properties: The reduction of dithiothreitol to a typical disulfide bond consists of two consecutive sulfhydryl disulfide bond exchange reactions: the intermediate state formed by the first reaction is very unstable, because the second sulfhydryl group on the DTT tends to connect with the oxidized sulfur atom, so that the intermediate state is quickly converted into the cyclic oxidation structure of the DTT, thus completing the reduction of the disulfide bond. Because it is easy to be oxidized by air, the stability of dithiothreitol (DTT) is poor; However, frozen storage or treatment in inert gas can prolong its service life. Due to the low nucleophilicity of protonated sulfur, the effective reducibility of DTT decreases with the decrease of pH value; Tris (2-carboxyethyl) phosphineHCl (TCEP hydrochloride) can be used as a substitute for DTT at low pH, and is more stable than DTT.

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