Dithioerythritol CAS 6892-68-8

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  • Appearance: White powder 
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available

Basic Info of Dithioerythritol

What is Dithioerythritol?

Dithioerythritol, also known as dithioerythritol (DTE), is a stereoisomer of dithiothreitol (DTT). The two hydroxyl groups of DTT are in the threo configuration, and the two hydroxyl groups in DTE are in the erythro configuration.

Dithiothreitol (DTT) is a generic name for a small molecule REDOX reagent, also known as cleland reagent. Its oxidized form is a 6-membered ring of disulfide bonds. The reagent is usually used in its racemic form because both enantiomers are reactive. Its name comes from the four-carbon sugar threosaccharide. DTT has a differential isomer (‘ sister ‘) compound, erythritol dithione (DTE).

Disulfide erythritol (DTE) is a sulfur-containing sugar derived from the corresponding 4-carbon monosaccharide erythritol. It is a differential isomer of dithiothreitol (DTT). The formula for DTE is C 4 H 10 O 2 S 2.

Like DTT, DTE is an excellent reducing agent, although its standard reduction potential is less negative, i.e., DTE is slightly less effective at reduction than DTT. This may be because the orientation of OH groups in their circular disulfide form (oxidized form) is less stable due to greater spatial repulsion than their orientation in the disulfide form of DTT. In the disulfide form of DTT, these hydroxyl groups are trans to each other, whereas in DTE they are cis to each other.

Dithioerythritol Uses

  1. Reagent for reducing disulfide bond. In the process of SDS- polyacrylamide gel electrophoresis, the oxidation of mercapto containing proteins was prevented. Disulfide bond breaking in proteins.
  2. 1,4-dithioerythritol is a Michael reaction receptor; Inducers of enzymes that prevent carcinogenesis: reactivity with sulfhydryl groups.
  3. DTE can be used as a reducing agent and deprotection agent for SULFHYDRYLATED DNA. It is also commonly used for the reduction of disulfide bonds in proteins to prevent intramolecular or intermolecular disulfide bonds formed between cysteines in proteins.

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The Preparation Method of Dithioerythritol

One of the difficulties in synthesizing DTE is the construction of erythro-configured dihydroxyl groups, and there are few literature reports on the synthesis of dithioerythroxenol. CN201611235712.7 performs cis addition on cis olefins to obtain products of erythro configuration, and successfully developed a synthetic method for preparing dithioerythritol. The synthetic method has a short route, can obtain better yield, and has good application value.

A method for preparing dithioredoxanal alcohol, comprising the following steps:

(a) Cis-1,4-dichloro-2-butene is dissolved in the first reaction solvent, and under low temperature conditions, cis-bishydroxylation reaction occurs with potassium permanganate to obtain formula (I) 1, 4-Dichloro-2,3-dibutanol;

(b) Dissolving the 1,4-dichloro-2,3-dibutanol of formula (I) prepared in step (a) in the second reaction solvent, adding an appropriate organic base, and performing an esterification reaction with acetic anhydride, 1,4-dichloro-2,3-diacetate of formula (II) is obtained;

(c) In the third reaction solvent, the 1,4-dichloro-2,3-diacetate of formula (II) prepared in step (b) is reacted with potassium thioacetate under the catalysis of sodium iodide. Nucleophilic substitution reaction to obtain 1,4-dithioacetyl-2,3-acetate of formula (III);

(d) In the fourth reaction solvent, the 1,4-dithioacetyl-2,3-acetate of formula (III) prepared in step (c) undergoes a hydrolysis reaction with an acidic reagent to obtain the target product formula (IV) ) dithioredoxanol.

The reaction process is shown in route (1):

Quality Control of Dithioerythritol

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