Glyceraldehyde


Glyceraldehyde
Glyceraldehyde
Identifiers
CAS number 367-47-5 YesY
Jmol-3D images Image 1
Properties[1]
Molecular formula C3H6O3
Molar mass 90.08 g mol−1
Density 1.455 g/cm³
Melting point

145 °C, 418 K, 293 °F

Boiling point

140-150°C at 0.8 mmHg

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 hydroxymethylene group changed to an aldehyde.

Contents

Structure

Glyceraldehyde has chiral center and therefore exists as two different enantiomers with opposite optical rotation:

  • R from Latin rectus meaning "right", or
  • S from Latin sinister meaning "left"
d-glyceraldehyde
(R)-glyceraldehyde
(+)-glyceraldehyde
l-glyceraldehyde
(S)-glyceraldehyde
(−)-glyceraldehyde
Fischer projection D-glyceraldehyde L-glyceraldehyde
Skeletal formula D-glyceraldehyde L-glyceraldehyde
Ball-and-stick model D-glyceraldehyde L-glyceraldehyde

While the optical rotation of glyceraldehyde is (+) for R and (−) for S, this is not true for all monosaccharides. The stereochemical rotation can only be determined by the chemical structure, whereas the optical rotation can only be determined empirically (by experiment).
It was by a lucky guess that the molecular d- geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by X-ray crystallography in 1951.

Nomenclature

In the d/l system, glyceraldehyde is used as the configurational standard for carbohydrates. Monosaccharides with a conformation identical to (R)-glyceraldehyde at the last stereocentre, for example C5 in glucose, are assigned the stereo-descriptor d-. Those similar to (S)-glyceraldehyde are assigned an l-.

Synthesis and biochemical role

Glyceraldehyde can be prepared, along with dihydroxyacetone, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst. Dihydroxyacetone, the simplest ketose, is an isomer of glyceraldehyde. Interconversion of the phosphates of these two compounds, catalyzed by the enzyme triosephosphate isomerase, is an important intermediate step in glycolysis.

See also

References

  1. ^ Merck Index, 11th Edition, 4376

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Look at other dictionaries:

  • Glyceraldehyde — Glycéraldéhyde Glycéraldéhyde …   Wikipédia en Français

  • Glycéraldéhyde — Glycéraldéhyde …   Wikipédia en Français

  • glycéraldéhyde — ● glycéraldéhyde nom masculin Dénomination courante du dihydroxy 2,3 propanal, le plus simple des aldoses contenant un atome de carbone chiral. (Le glycéraldéhyde peut se transformer en dihydroxyacétone, et le mélange de ces deux composés… …   Encyclopédie Universelle

  • glyceraldehyde — [glis΄ər al′də hīd΄] n. the simplest aldehyde sugar, C3H6O3, used as the standard reference for carbohydrate structure and produced in the body by the oxidation of sugars …   English World dictionary

  • glyceraldehyde — /glɪsəˈrældəhaɪd/ (say glisuh ralduhhuyd) noun a crystalline aldose, C3H6O3, from which simple sugars are formally derived, having two enantiomers, dextrorotatory (D glyceraldehyde) and laevorotatory (L glyceraldehyde), which are the basis for… …   Australian English dictionary

  • glyceraldehyde — glicerolio aldehidas statusas T sritis chemija formulė H(CHOH)₂CHO atitikmenys: angl. glyceraldehyde rus. глицериновый альдегид ryšiai: sinonimas – gliceraldehidas sinonimas – 2,3 dihidroksipropanalis sinonimas – aldotriozė …   Chemijos terminų aiškinamasis žodynas

  • glyceraldehyde — noun Etymology: glyceric acid + aldehyde Date: 1882 a sweet crystalline compound C3H6O3 that is formed as an intermediate in carbohydrate metabolism by the breakdown of sugars and that yields glycerol on reduction …   New Collegiate Dictionary

  • glyceraldehyde — /glis euh ral deuh huyd /, n. Biochem. a white, crystalline, water soluble solid, C3H6O3, that is an intermediate in carbohydrate metabolism and yields glycerol on reduction. Also called glyceric aldehyde. [1880 85; GLYCER(IN) + ALDEHYDE] * * * …   Universalium

  • glyceraldehyde — noun The aldotriose 2,3 dihydroxypropanal formed by oxidation of glycerol …   Wiktionary

  • glyceraldehyde — A triose and the simplest optically active aldose; the dextrorotatory isomer is taken as the structural reference point for all d compounds, the levorotatory isomer for all l compounds. SYN: glyceric aldehyde. * * * glyc·er·al·de·hyde .glis ə ral …   Medical dictionary


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