Dithioerythritol (DTE) is a sulfur containing sugar derived from the corresponding 4-carbon
monosaccharide
Monosaccharides (from Greek ''monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built.
They are usually colorless, water-solub ...
erythrose
Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose; it is a diastereomer of D -threose.
Erythrose was first isolated in 1849 ...
. It is an
epimer
In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is ...
of
dithiothreitol
Dithiothreitol (DTT) is the common name for a small-molecule redox reagent also known as Cleland's reagent, after W. Wallace Cleland. DTT's formula is C4H10O2S2 and the chemical structure of one of its enantiomers in its reduced form is shown on ...
(DTT). The molecular formula for DTE is C
4H
10O
2S
2.
Like DTT, DTE makes an excellent
reducing agent
In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ).
Examples of substances that are commonly reducing agents include the Earth meta ...
, although its standard
reduction potential
Redox potential (also known as oxidation / reduction potential, ''ORP'', ''pe'', ''E_'', or E_) is a measure of the tendency of a chemical species to acquire electrons from or lose electrons to an electrode and thereby be reduced or oxidised respe ...
is not quite as negative, i.e., DTE is slightly less effective at reducing than 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
Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivity of ions ...
than their orientation in the disulfide-bonded form of DTT. In the disulfide-bonded form of DTT, these
hydroxyl groups
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
are
''trans'' to each other, whereas they are ''cis'' to each other in DTE.
References
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External links
*{{Commonscatinline
Thiols
Vicinal diols