Threose

Threose is an aldotetrose monosaccharide with four carbon atoms and two stereogenic centers. Its D- and L-enantiomers differ in configuration at every stereogenic center.

Monosaccharide: A simple carbohydrate that cannot be hydrolyzed into smaller carbohydrate molecules. Threose is one sugar unit, not a chain of linked sugars.
Open-chain form: A molecular form in which a molecule’s carbon framework is not closed into a ring. Open-chain threose displays the aldehyde group that defines it as an aldose.
Erythrose: An aldotetrose whose two hydroxyl groups on adjacent stereogenic carbons lie on the same side in a Fischer projection. Erythrose is the diastereomer distinguished from threose by configuration at one stereogenic center.
Threose nucleic acid: A synthetic genetic polymer whose backbone is built from repeating threose-derived units. Threose supplies the sugar framework in this alternative to natural nucleic acids.
Aldose: A monosaccharide whose open-chain form contains an aldehyde group. Threose belongs to this class because its open-chain form has an aldehyde.
Hemiacetal: A functional group formed when an alcohol adds to an aldehyde or ketone carbonyl. Intramolecular addition of a hydroxyl group can close threose into a cyclic hemiacetal.
Threitol: A four-carbon sugar alcohol related to threose by reduction of its aldehyde group. Reduction changes threose’s aldehyde into an alcohol, yielding a related but distinct compound.
Xeno nucleic acid: A nucleic acid analogue with a genetic backbone different from DNA and RNA. Threose nucleic acid is one member of this broader class of genetic polymers.
Tetrose: A monosaccharide containing four carbon atoms. The four-carbon backbone places threose in this size class.
Mutarotation: A change in a sugar solution’s optical rotation as its anomeric forms interconvert. Threose’s cyclic forms can interconvert through its open-chain form.

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DiastereomerRelated: Its configurations provide a compact example of multiple diastereomeric sugar forms.