DL-Dithiothreitol CAS 3483-12-3

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DL-Dithiothreitol (DTT for short) is a small molecule organic reducing agent with the chemical formula C4H10O2S2. It is a linear molecule in the reduced state, and becomes a six membered ring structure containing disulfide bonds after oxidation. The name dithiothreitol derives from threose, a four carbon monosaccharide. The isomer of DTT is dithioerythritol (DTE), which is the C3 epimer of DTT. Soluble in water.

Because it is easy to be oxidized by air, the stability of DTT is poor; However, freezing storage or treatment in inert gas can prolong its service life. Due to the low nucleophilicity of protonated sulfur, the effective reduction of DTT decreases with the decrease of pH; Tris (2-carboxyethyl) phosphate HCl (TCEP hydrochloride) can be used as a substitute for DTT at low pH and is more stable than DTT.

DL Dithiothreitol (DTT) is a small molecule organic reducing agent with the chemical formula C4H10O2S2. Due to its strong reducibility and multifunctionality, it has a wide range of applications in biotechnology, biomedicine, chemical experiments, environmental protection, food, agriculture and other fields.

Biotechnology field

 

Protein lysis and disulfide bond reduction:
The core application of DTT in biotechnology is as a protein lysis reagent. The disulfide bond (Cys Cys) in proteins is an important covalent bond that maintains its tertiary structure. DTT reduces disulfide bonds to thiol groups (- SH) through a two-step continuous thiol disulfide bond exchange reaction, thereby disrupting the natural conformation of proteins. For example, before SDS-PAGE electrophoresis, DTT is used to reduce protein disulfide bonds to ensure the accuracy of protein separation. In addition, DTT can also be used in proteomics research to assist in the separation and analysis of complex protein mixtures.
The reducibility of DL-Dithiothreitol is significantly affected by pH value and only works when pH>7. This is because only protonated thiol salt anions have reactivity, and the pKa of thiol groups is generally 8.3. Therefore, DTT is often used under alkaline conditions to ensure its reduction efficiency.

 

DNA synthesis and modification
DTT acts as a reducing and deprotection agent in DNA synthesis. The thiolated DNA terminal sulfur atoms are prone to dimerization in solution, especially in the presence of oxygen, which can reduce the efficiency of coupling reactions. For example, in DNA biosensors, DTT can reduce DNA dimerization and improve fixation efficiency. In addition, DTT can also be used to remove protective groups during DNA synthesis, ensuring the purity of the synthesized products.
RNA experiment assistance
DTT has an inhibitory effect on RNA enzyme activity in RNA experiments. RNases are widely present in the environment and are highly capable of degrading RNA samples. DTT protects RNA samples by denaturing and inactivating the disulfide bonds in RNase proteins. For example, in RNA library construction and amplification experiments, the addition of DTT can significantly improve RNA integrity and experimental success rate.

Biomedical field

 

Vaccine formulations and nucleic acid testing:
DTT acts as a protein thiol protectant in vaccine formulations, preventing cysteine residues from forming intramolecular and intermolecular disulfide bonds, thereby maintaining the natural conformation and activity of vaccine proteins. For example, in the development of COVID-19 vaccine, DTT was used to optimize the stability of antigen protein.
In nucleic acid testing, DTT is also used to inhibit RNase activity and ensure the integrity of RNA samples. In addition, DTT can also be used for protein removal during nucleic acid extraction to improve nucleic acid purity.

 

Detoxification of cellular tissues and radiation protection:
DTT has antioxidant properties and can protect cells and tissues from oxidative damage. For example, in radiation therapy, DTT can serve as a radiation protective agent to reduce radiation damage to normal cells. In addition, DTT can also be used to treat certain diseases caused by ions or organic toxins, such as cystinosis.
Red blood cell processing and blood type identification:
DTT plays an important role in red blood cell processing. For example, DTT can cleave the extracellular disulfide bond of CD38 molecule, denature the CD38 antigen, prevent it from binding to CD38 monoclonal antibody, and provide safe blood for patients receiving CD38 monoclonal antibody treatment. In addition, DTT can also break the disulfide bonds of cold autoantibody IgM molecules, eliminate their interference in blood type identification, and ensure the accuracy of blood type identification.

Chemical Experiment Field

 

Enzyme activity protection and inhibitors
DTT can protect the reducing groups on enzyme molecules, maintain a reducing environment, and stabilize enzyme activity. For example, in enzymatic reactions, the addition of DTT can prolong the enzyme's lifespan and improve reaction efficiency. In addition, DTT can also serve as a specific inhibitor of enzymes for studying their mechanisms of action.
Measure enzyme activity
DTT plays an important role in enzyme activity determination. For example, when measuring the activity of certain oxidoreductases, DTT can act as an electron donor or acceptor, participating in enzymatic reactions and indirectly measuring enzyme activity.

Environmental protection field

 

Wastewater treatment and pollutant degradation:
DL-Dithiothreitol can be used in wastewater treatment to remove heavy metal ions and organic pollutants. For example, DTT can form stable complexes with heavy metal ions, thereby reducing their toxicity. In addition, DTT can also be used to degrade certain recalcitrant organic pollutants, such as dyes and pesticides.
Synthesis of Gold Nanomaterials:
DTT plays an important role in the synthesis of gold nanomaterials. For example, in the synthesis of gold nanoparticles, DTT can serve as a reducing agent and stabilizer to control the size and morphology of the gold nanoparticles. In addition, DTT can also be used to synthesize other high-end materials, such as quantum dots and nanowires.

Food and cosmetics industry

 

Antioxidants and preservatives:
DTT has antioxidant and preservative effects in the food additive and cosmetics industries. For example, adding DTT to food can extend its shelf life and prevent food oxidation and spoilage. In cosmetics, DTT can protect active ingredients from oxidative damage and improve product stability.
Food quality improvement:
DTT can also be used for improving food quality. For example, in bread making, DTT can improve the rheological properties of dough, increase the volume and taste of bread. In meat processing, DTT can be used to tenderize meat, improve the tenderness and juiciness of meat.

Agriculture and Industry

 

Agricultural applications:
DTT has potential application value in agriculture. For example, DTT can be used to prevent protein denaturation in plants and improve their stress resistance. In addition, DTT can also be used for the research and development of pesticide adjuvants, improving the stability and effectiveness of pesticides.
Industrial Electroplating and Daily Chemicals:
DTT can be used for metal surface treatment in industrial electroplating, improving the adhesion and corrosion resistance of the plating layer. In daily chemical products, DTT can be used in the formula of shampoo, shower gel and other products to improve the cleaning effect and mildness of the products.

For the new synthesis method of dithiothreitol, the raw material consumption is calculated according to the theoretical product yield of 277.6g, including the following steps:

a. Add 162.5g (1.80mol) of 1,4-butenediol into the reaction kettle, slowly drip 316.8g (1.98mol) of liquid bromine under the stirring condition, stir for 16 hours under the temperature of 25 ℃ after dropping, stand still for layering, take the supernatant, and then obtain 2,3-dibromo-1,4-butanediol. Store it in a tank with the temperature lower than 30 ℃ for standby;

b. In the supernatant obtained in step a, 651.2g (4.88mol) of sodium hydroxide solution with a mass percent concentration of 30% is added, and the reaction is stirred at a temperature lower than 20 ℃ for 16 hours to obtain ethylene oxide;

c. Add 155.67g (2.045mol) of thioacetic acid into the reaction solution obtained in step b, stir and react for 20 hours, distill under reduced pressure, and crystallize to obtain dithiothreitol diacetate;

d. In the crystallization obtained in step c, 190.9g (1.432mol) of sodium hydroxide solution with a mass percent concentration of 30% is added, stirred for reaction for 4 hours, cooled to room temperature, adjusted pH to 7.5~8.0 with hydrochloric acid solution with a mass percent concentration of 3%, extracted with 300mL of ethyl acetate, combined the organic layers, distilled under normal pressure to remove ethyl acetate, and then distilled the residual concentrated solution under reduced pressure at a vacuum of 15mmHg and a temperature of 180~200 ℃, The distillate with temperature between 130~140 ℃ was collected and cooled to room temperature to obtain 100g of white solid dithiothreitol with yield of 36.02%.

DL-Dithiothreitol is a strong reducing agent, and its reducibility is largely due to the conformational stability of its oxidized six membered ring (containing disulfide bond). Its redox potential is -0.33 V at pH 7. The reduction of a typical disulfide bond by dithiothreitol consists of two consecutive mercapto disulfide bond exchange reactions.

Among them, the intermediate state formed in the first step of the 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 transformed into the cyclic oxidation structure of the DTT, thus completing the reduction of the disulfide bond.

The reducing power of DTT is affected by the pH value, and it can only play a reducing role when the pH value is greater than 7. This is because only the protonated mercaptan anion (- S –) has reactivity, while mercaptan (- SH) does not; The pKa of thiol group is generally~8.3.

Because it is easy to be oxidized by air, the stability of DTT is poor; However, freezing storage or treatment in inert gas can prolong its service life. Due to the low nucleophilicity of protonated sulfur, the effective reduction of DTT decreases with the decrease of pH; Tris (2-carboxyethyl) phosphate HCl (TCEP hydrochloride) can be used as a substitute for DTT at low pH and is more stable than DTT.

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