DL Dithiothreitol CAS 3483-12-3

DL-Dithiothreitol (DTT) is a small molecule organic reducing agent with the chemical formula C4H10O2S2. It is mainly used as a protein lysis reagent and is applied in the field of biotechnology. Although it is a strong reducing agent, it is incompatible with general strong oxidants. However, it should be noted that this product is sensitive to heat. and easily oxidized when exposed to air for a long time. Therefore, long-term storage should be carried out in a frozen environment of -20 to -10 ℃, or in an inert gas environment to extend its service life.

Dithiothreitol is a linear molecule in the reduced state, and after oxidation, it becomes a hexagonal cyclic structure containing disulfide bonds. The isomer of DTT is dithioerythritol (DTE), which is the C3 isomer of DTT.

What is the reducibility of dithiothreitol?

DTT is a strong reducing agent, and its reducibility is largely due to the conformational stability of its six membered ring (containing disulfide bonds) in its oxidized state. Its redox potential is -0.33 volts at pH 7. The reduction of a typical disulfide bond proceeds by two sequential thiol-disulfide exchange reactions and is illustrated below.

Among them, the intermediate state formed in the first step of the reaction is very unstable because the second thiol group on the DTT tends to connect with the oxidized sulfur atom, quickly converting the intermediate state into the cyclic oxidation structure of the DTT, thereby completing the reduction of the disulfide bond.

The reducing power of DTT is limited to pH values above 7, since only the negatively charged thiolate form -S− is reactive (the protonated thiol form -SH is not); the pKa of the thiol groups is 9.2 and 10.1.

What are the applications of DTT?

One of the uses of DL-1,4-Dithiothreitol is as a reducing agent and deprotecting agent for sulfhydryl DNA.The terminal sulfur atoms of thiolated DNA have a tendency to form dimers in solution, especially in the presence of oxygen. Dimerization greatly lowers the efficiency of subsequent coupling reactions such as DNA immobilization on gold in biosensors.Adding DTT to DNA solution and removing it after a period of reaction can reduce DNA dimerization.

DTT is also commonly used for the reduction of disulfide bonds in proteins, which can be used to prevent the formation of intramolecular or intermolecular disulfide bonds between cysteine residues in proteins.But it needs to be done under the condition of protein denaturation.DTT is oftentimes used along with sodium dodecylsulfate in SDS-PAGE to further denature proteins by reducing their disulfide bonds to allow for better separation of proteins during electrophoresis.At the same time, in the presence of DTT, the different reduction speed of disulfide bonds can judge the depth of disulfide bond embedding of protein.
Because of the ability to reduce disulfide bonds, DTT can be used to denature CD38 on red blood cells.

In some cases, DL-Dithiothreitol can also serve as an oxidant. Compared with other products such as glutathione, the two sulfur atoms of DTT may form disulfide bonds to different sulfur atoms. In rare cases, it may form non cyclized DTT adducts, but there will be no mixed disulfide present.

What are the characteristics of this product?

As I said above, DTT is easily oxidized by air, and low temperature will only slow down the speed of air oxidation and will not stop the oxidation reaction, so if your storage is simple, it is not suitable to store this product for a long time. And,Oxidized DTT exhibits a strong absorbance peak at 280 nm.

Since thiols are less nucleophilic than their conjugate bases, thiolates, DTT becomes a less potent nucleophile as the pH falls.However, Tris(2-carboxyethyl)phosphine HCl (TCEP HCl) can be used as a substitute for DTT at low pH, and it is also more stable than DTT.

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