Threitol is the
chiral
Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek language, Greek (''kheir''), "hand", a familiar chiral object.
An object or a system is ''chiral'' if it is dist ...
four-carbon
sugar alcohol
Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group attached to each carbon atom. They are white, water-soluble solids that c ...
with the molecular formula C
4H
10O
4. It is primarily used as an intermediate in the chemical synthesis of other compounds. It exists in the
enantiomorphic forms D-threitol and L-threitol, the reduced forms of D- and L-
threose
Threose is a four-carbon monosaccharide with molecular formula C4H8O4. It has a terminal aldehyde group, rather than a ketone, in its linear chain and so is considered part of the aldose family of monosaccharides. The threose name can be used to ...
. It is the
diastereomer
In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have di ...
of
erythritol
Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L- erythrose and one of the two reduced forms of erythrulose. It is used as a food ad ...
, which is used as a sugar substitute.
In living organisms, threitol is found in the
edible fungus ''
Armillaria mellea
''Armillaria mellea'', commonly known as honey fungus, is an edible basidiomycete fungus in the genus ''Armillaria''. It is a plant pathogen and part of a cryptic species complex of closely related and Morphology (biology), morphologically simila ...
''.
It serves as a cryoprotectant (antifreeze agent) in the Alaskan beetle ''
Upis ceramboides''.
See also
*
Antifreeze protein
Antifreeze proteins (AFPs) or ice structuring proteins refer to a class of polypeptides produced by certain animals, plants, fungi and bacteria that permit their survival in temperatures below the freezing point of water. AFPs bind to small ...
*
Dithiothreitol
Dithiothreitol (DTT) is an organosulfur compound with the formula . A colorless compound, it is classified as a dithiol and a diol. DTT is redox reagent also known as Cleland's reagent, after W. Wallace Cleland. The reagent is commonly used in ...
, a
thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...
derivative of threitol
References
External links
*
Sugar alcohols
Tetroses
Tetrols
{{Carbohydrate-stub