Glyceraldehyde

Glyceraldehyde
Names
	IUPAC name Glyceraldehyde
	Systematic IUPAC name 2,3-Dihydroxypropanal
	Other names Glyceraldehyde; Glyceric aldehyde; Glyceral
Identifiers
CAS Number	56-82-6 (racemic) ; 453-17-8 (R) ; 497-09-6 (S) ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	731 ;
ECHA InfoCard	100.000.264
PubChem CID	751;
UNII	DI19XSG16H (racemic) ; 41A680M0WB (R) ; GI7U82BL5A (S) ;
CompTox Dashboard (EPA)	DTXSID90861586 ;
	InChI InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 Key: MNQZXJOMYWMBOU-UHFFFAOYSA-N ; InChI=1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 Key: MNQZXJOMYWMBOU-UHFFFAOYAU;
	SMILES O=CC(O)CO; OCC(O)C=O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

Glyceraldehyde (glyceral) 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 glycerol and aldehyde, as glyceraldehyde is glycerol with one alcohol group oxidized to an aldehyde.

Structure

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

In the D/L nomenclature, either D from Latin Dexter meaning "right", or L from Latin Laevo meaning "left"
In the R/S nomenclature, either 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
Skeletal formula
Ball-and-stick model

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.^[2]

Nomenclature

In the D/L system, glyceraldehyde is used as the configurational standard for carbohydrates.^[3] 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-.

Chemical synthesis

Glyceraldehyde can be prepared, along with dihydroxyacetone, by the mild oxidation of glycerol, for example with hydrogen peroxide^[4] and a ferrous salt as catalyst.^{[citation needed]}

Its cyclohexylidene acetal can also be produced by oxidative cleavage of the bis(acetal) of mannitol.^[5]

Biochemistry

The enzyme glycerol dehydrogenase (NADP⁺) has two substrates, glycerol and NADP⁺, and 3 products, D-glyceraldehyde, NADPH and H+.^[6]

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.

References

^ Merck Index, 11th Edition, 4376
^ 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.
^ "22.03: The D and L Notation". Chemistry LibreTexts. 2015-03-19. Retrieved 2022-01-09.
^ Wu, Gongde; Wang, Xiaoli; Jiang, Taineng; Lin, Qibo (2015-11-27). "Selective Oxidation of Glycerol with 3% H2O2 Catalyzed by LDH-Hosted Cr(III) Complex". Catalysts. 5 (4): 2039–2051. doi:10.3390/catal5042039. ISSN 2073-4344.
^ 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.
^ 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.

[1] Merck Index, 11th Edition, 4376

[2] 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.

[3] "22.03: The D and L Notation". Chemistry LibreTexts. 2015-03-19. Retrieved 2022-01-09.

[4] Wu, Gongde; Wang, Xiaoli; Jiang, Taineng; Lin, Qibo (2015-11-27). "Selective Oxidation of Glycerol with 3% H2O2 Catalyzed by LDH-Hosted Cr(III) Complex". Catalysts. 5 (4): 2039–2051. doi:10.3390/catal5042039. ISSN 2073-4344.

[5] 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.

[6] 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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