Glyceraldehyde
Encyclopedia : G : GL : GLY : Glyceraldehyde
Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. It is the simplest of all common aldoses. It is a sweet colorless crystalline solid that is an intermediate compound in carbohydrate metabolism. The word comes from combining glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxide changed to an aldehyde.
Glyceraldehyde has a chiral centre and therefore exists in two different conformations with opposite steriochemical rotation:
- R from Latin rectus meaning upright, or
- S from Latin sinister meaning left
Monosaccharides with an identical conformation at the last stereocentre (eg. C5 for glucose) to (R)-glyceraldehyde are assigned the stereo-descriptor D, those similar to (S)-glyceraldehyde are assigned a L. Both, D and L, should be small capital letters.
Glyceraldehyde can be prepared, along with dihydroxyacetone, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst.
It was by a lucky guess that the D molecular geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by x-ray crystallography in 1951.
See also
External links
- [Structure of D-glyceraldehyde]
- [Chin. Chem. Soc., Vol. 46(3) 283 (1999)] On the Assignment of Anomeric Configuration (pdf)
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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