Glyceraldehyde

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Glyceraldehyde
Glyceraldehyde Glyceraldehyde v2.svg
Glyceraldehyde
D-glyceraldehyde D-Glyceraldehyde 2D Fischer.svg
D-glyceraldehyde
Names
IUPAC name
Glyceraldehyde [1]
Systematic IUPAC name
2,3-Dihydroxypropanal
d-glycero-Triose [2]
Other names
Glyceraldehyde
Glyceric aldehyde
Glyceral
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.264 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 Yes check.svgY
    Key: MNQZXJOMYWMBOU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2
    Key: MNQZXJOMYWMBOU-UHFFFAOYAU
  • O=CC(O)CO
  • OCC(O)C=O
Properties [3]
C3H6O3
Molar mass 90.078 g·mol−1
Density 1.455 g/cm3
Melting point 145 °C (293 °F; 418 K)
Boiling point 140 to 150 °C (284 to 302 °F; 413 to 423 K) at 0.8 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glyceraldehyde (glyceral) is a triose monosaccharide with chemical formula C 3 H 6 O 3. 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 glycerol and aldehyde, as glyceraldehyde is glycerol with one alcohol group oxidized to an aldehyde. [4]

Contents

Structure

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

D-glyceraldehyde
(R)-glyceraldehyde
(+)-glyceraldehyde		L-glyceraldehyde
(S)-glyceraldehyde
(−)-glyceraldehyde
Fischer projection D-Glyceraldehyde 2D Fischer.svg L-Glyceraldehyde 2D Fischer.svg
Skeletal formula D-glyceraldehyde-2D-skeletal.svg L-glyceraldehyde-2D-skeletal.svg

While the optical rotation of glyceraldehyde is (+) for R and (−) for S, this is not true for all monosaccharides. The stereochemical configuration can only be determined from 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. [5]

Aqueous and concentrated solutions of glyceraldehyde

The description above focuses on classification of isomers, but the glyceraldehyde is subject to a further complications: the tendency of hydroxy-aldehydes to exist as hydrates. NMR measurements indicate that in aqueous solution, glyceraldehyde exists in a hydrate owing to this reaction:

HOCH2CH(OH)CHO + H2O ⇌ HOCH2CH(OH)CH(OH)2

The same study indicates that concentrated ("syrupy") forms of glyceraldehyde exist as dimers, indicating hemiacetal formation. [6]

Nomenclature

In the D/L system, glyceraldehyde is used as the configurational standard for carbohydrates. [7] Monosaccharides with an absolute configuration 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 reactions

Glyceraldehyde can be prepared from acetals of acrolein (CH2=CHCHO) in two steps, oxidation [8] followed by hydrolysis of the acetal. [9] Its cyclohexylidene acetal can also be produced by oxidative cleavage of the bis(acetal) of mannitol. [10]

Glyceraldehyde is a precursor to four-carbon sugars (tetroses) via cyanation followed by hydrolysis of the cyanohydrin: [4]

HOCH2CH(OH)CH(OH)CN + 2 H2O → HOCH2CH(OH)CH(OH)CO2H + NH3
HOCH2CH(OH)CH(OH)CO2H + 2 H2 → HOCH2CH(OH)CH(OH)CH2OH + H2O

Biochemistry

The enzyme glycerol dehydrogenase (NADP+) has two substrates, glycerol and NADP+, and 3 products, D-glyceraldehyde, NADPH and H+. [11]

The interconversion of the phosphates of glyceraldehyde (glyceraldehyde 3-phosphate) and dihydroxyacetone (dihydroxyacetone phosphate), catalyzed by the enzyme triosephosphate isomerase, is an intermediate step in glycolysis.

See also

References

  1. ↑ https://iupac.qmul.ac.uk/BlueBook/P10.html#t1002
  2. ↑ https://iupac.qmul.ac.uk/BlueBook/P10.html#t1002
  3. ↑ Merck Index, 11th Edition, 4376
  4. 1 2 "Molecule of the Week: D-Glyceraldehyde". C&E News. 2023.
  5. ↑ Bijvoet, J. M.; Peerdeman, A. F.; Van Bommel, A. J. (1951). "Determination of the Absolute Configuration of Optically Active Compounds by Means of X-Rays". Nature. 168 (4268): 271–272. Bibcode:1951Natur.168..271B. doi:10.1038/168271a0.
  6. ↑ Angyal, SJ; Wheen, RG (1980). "The Composition of Reducing Sugars in Aqueous Solution : Glyceraldehyde, Erythrose, Threose". Australian Journal of Chemistry. 33 (5): 1001. doi:10.1071/CH9801001.
  7. ↑ "22.03: The D and L Notation". Chemistry LibreTexts. 2015-03-19. Retrieved 2022-01-09.
  8. ↑ Witzemann, E. J.; Llloyd Evans, Wm.; Hass, Henry; Schroeder, E. F. (1931). "dl-Glyceraldehyde Ethyl Acetal". Organic Syntheses. 11: 52. doi:10.15227/orgsyn.011.0052.
  9. ↑ Witzemann, E. J.; Llloyd Evans, Wm.; Hass, Henry; Schroeder, E. F. (1931). "dl-Glyceraldehyde". Organic Syntheses. 11: 50. doi:10.15227/orgsyn.011.0050.
  10. ↑ Dhatrak, N. R.; Jagtap, T. N.; Shinde, A. B. (2022). "Preparation of 1,2:5,6-Di-O-cyclohexylidene-D-mannitol and 2,3-Cyclohexylidene-D-glyceraldehyde". Organic Syntheses. 99: 363–380. doi: 10.15227/orgsyn.099.0363 . S2CID   254320929.
  11. ↑ Kormann, Alfred W.; Hurst, Robert O.; Flynn, T.G. (1972). "Purification and properties of an NADP+-dependent glycerol dehydrogenase from rabbit skeletal muscle". Biochimica et Biophysica Acta (BBA) - Enzymology. 258 (1): 40–55. doi:10.1016/0005-2744(72)90965-5. PMID   4400494.
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