D-Glyceraldehyde

Description

D-(+)-Glyceraldehyde is an intermediate in carbohydrate metabolism. It is phosphorylated by triose kinase to produce D-glyceraldehyde 3-phosphate, an intermediate in glycolysis, gluconeogenesis, photosynthesis, and other metabolic pathways.

Description

D-Glyceraldehyde, a triose and the simplest aldose (aldehyde sugar), is an intermediate in fructose metabolism. It occurs in all living organisms, including humans. Its enantiomer, L-glyceraldehyde1, is related to the natural amino acids; but it does not occur in nature.
Racemic glyceraldehyde, along with dihydroxyacetone2, can be synthesized via the hydrogen peroxide oxidation of glycerol. Further oxidation of rac-glyceraldehyde produces rac-glyceric acid3 and eventually one- and two-carbon compounds.
D-Glyceraldehyde is an important starting material for the classic Kiliani–Fischer synthesis, which is used to build larger sugars from smaller ones. In this synthesis, D-glyceraldehyde reacts with cyanide ion to add a carbon atom at the aldehyde position. The nitrile group is then hydrolyzed and catalytically hydrogenated to produce the tetroses D-erythrose4 and D-threose5. Further iterations of the Kiliani–Fischer synthesis lead to higher aldoses.
D-Glyceraldehyde is also involved in shortening aldose chains, as exemplified by the Wohl degradation. It essentially accomplishes the reverse of the Kiliani–Fischer synthesis, so that D-erythrose and D-threose can be degraded to D-glyceraldehyde in a three-step process that, like Kiliani–Fischer, proceeds through a nitrile intermediate.
For additional information, see the ScienceDirect topic page on D-glyceraldehyde. And a question for readers: Crystalline D-glyceraldehyde has a relatively high melting point of 145 °C—so why is the article of commerce a viscous syrup?
1. CAS Reg. No. 497-09-6. 2. CAS Reg. No. 96-26-4. 3. CAS Reg. No. 473-81-4. 4. CAS Reg. No. 583-50-6. 5. CAS Reg. No. 95-43-2.

Chemical properties

CLEAR ORANGE SYRUP

The Uses of D-Glyceraldehyde

D-Glyceraldehyde is the simplest of all aldoses and have been shown to be the one of the carbonyl metabolite of dietary fructose.

The Uses of D-Glyceraldehyde

D-(+)-Glyceraldehyde can be utilized as a reactant in the synthesis of:

• (S)-homophenylalanine by ruthenium oxidation of a 3-amino-1,2-diol generated via coupling of an amine, and α-hydroxyaldehyde.
• β- and γ-allenols via metal-catalyzed cyclization. Allenols are used as a key precursor for the preparation of enantiopure dihydropyrans and tetrahydrooxepines.
• Isopropylidene D-glyceraldehyde intermediate, which controls the chirality in the total synthesis of prostaglandins (PGE1).

What are the applications of Application

D-(+)-Glyceraldehyde is an intermediate in carbohydrate metabolism

Definition

ChEBI: The D-enantiomer of glyceraldehyde.

Purification Methods

enantiomer [453-17-8] is a syrup (70 + % H2O) with [] D +14o (c 2, H2O) and the dimethyl acetal has b 124-127 o/14mm and []15 +21o (c 18, H2O). [Beilstein 1 H 845, 1 IV 4114.]