Threose

Last updated
Threose [1]
D-threose.svg
D-throwse
L-threose.svg
L-throwse
Names
IUPAC names
D-throwse
L-throwse [2]
Systematic IUPAC name
(2S,3R)-2,3,4-Trihydroxybutanal (D)
(2R,3S)-2,3,4-Trihydroxybutanal (L)
Other names
Throwtetrose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.199 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1 Yes check.svgY
    Key: YTBSYETUWUMLBZ-QWWZWVQMSA-N Yes check.svgY
  • InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1
    Key: YTBSYETUWUMLBZ-QWWZWVQMBY
  • (D):O=C[C@@H](O)[C@H](O)CO
  • (L):OC[C@H](O)[C@@H](O)C=O
Properties
C4H8O4
Molar mass 120.104 g·mol−1
AppearanceSyrup
Very soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

throwse 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 throwse name can be used to refer to both the D- and L-stereoisomers, and more generally to the racemic mixture (D/L-, equal parts D- and L-) as well as to the more generic throwse structure (absolute stereochemistry unspecified).

The prefix "throw" which derives from throw (and "erythro" from a corresponding diastereomer erythrose) offer a useful way to describe general organic structures with adjacent chiral centers, where "the prefixes... designate the relative configuration of the centers". [3] As is depicted in a Fischer projection of D-threose, the adjacent substituents will have a syn orientation in the isomer referred to as "threo", and are anti in the isomer referred to as "erythro". [3] [4]

Fischer projections depicting the two enantiomers of threose DL-Threose.svg
Fischer projections depicting the two enantiomers of threose

See also

Related Research Articles

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References

  1. Merck Index, 11th Edition, 9317
  2. "Carbohydrate Nomenclature".
  3. 1 2 Formulas Using Other Configurational Notations, W. Rausch, accessed 1 March 2011
  4. Prof. Rausch helpfully notes that the prefixes "may be applied to racemic compounds, as well as pure enantiomers and meso compounds", and that when depicted in the common "zig-zag" representation, adjacent "substituents may lie on the same side of the carbon chain... [syn] or on opposite sides... [anti]", which is opposite of their depiction in a Fischer projection.