Glyceraldehyde

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Glyceraldehyde
Glyceraldehyde
D-glyceraldehyde
Names
IUPAC name
Glyceraldehyde
Systematic IUPAC name
2,3-Dihydroxypropanal
Other names
Glyceraldehyde
Glyceric aldehyde
Glyceral
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.000.264 Edit this at Wikidata
UNII
  • InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 checkY
    Key: MNQZXJOMYWMBOU-UHFFFAOYSA-N checkY
  • 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[1]
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).
☒N verify (what is checkY☒N ?)

Glyceraldehyde (glyceral) is a

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 D-glyceraldehyde L-glyceraldehyde
Skeletal formula D-glyceraldehyde L-glyceraldehyde
Ball-and-stick model D-glyceraldehyde L-glyceraldehyde

While the

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

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.

See also

References

  1. ^ Merck Index, 11th Edition, 4376
  2. doi:10.1038/168271a0
  3. ^ "22.03: The D and L Notation". Chemistry LibreTexts. 2015-03-19. Retrieved 2022-01-09.
  4. ISSN 2073-4344
    .
  5. S2CID 254320929
    .
  6. PMID 4400494
    .
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