glyseraldehydillä

Glyceraldehyde, known as glyseraldehyd on Finnish, is the simplest sugar alcohol containing an aldehyde functional group. It is a trihydroxy aldehyde with the molecular formula C3H6O3. Glyceraldehyde exists as two enantiomeric forms, D‑glyceraldehyde and L‑glyceraldehyde, distinguished by the spatial arrangement of the hydroxyl groups. The molecule can also be represented as a 1,2,3‑trihydroxy‑propan‑1‑al, with the aldehyde group at the terminal carbon.

In nature, glyceraldehyde is a key intermediate in carbohydrate metabolism. In the Embden‑Meyerhof‑Parnas pathway it is formed from the oxidative dephosphorylation of G6P by glucose‑6‑phosphate isomerase and subsequently converted to dihydroxyacetone phosphate by triose phosphate isomerase. The reversible reaction between glyceraldehyde‑3‑phosphate (G3P) and dihydroxyacetone phosphate is a central step of glycolysis and gluconeogenesis. G3P is further oxidized to 1,3‑bi­phosphate by glyceraldehyde‑3‑phosphate dehydrogenase, a step that generates NADH.

Glyceraldehyde is also involved in the pentose phosphate pathway, where it is produced from ribulose‑5‑phosphate. Its presence is crucial for the synthesis of ribose‑5‑phosphate, an essential component of nucleotides.

Beyond metabolism, glyceraldehyde can be isolated from carbohydrate hydrolysis and is utilized in chemical syntheses. Because of its aldehyde function, it readily reacts with amines to form imines or with nucleophiles to form additions, making it a versatile building block in medicinal chemistry and biocatalysis.

The compound is hygroscopic, crystalline at low temperatures, and unstable under acidic or basic conditions, decomposing to yield formic, acetic, and formaldehyde derivatives. Safety handling requires ventilation and avoidance of strong oxidizers due to its reducing nature.