Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH₂C(O)CH₂OPO₃^2-. This anion is involved in many

metabolic pathway In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell (biology), cell. The reactants, products, and Metabolic intermediate, intermediates of an enzymatic reaction are known as metabolites, which are ...

s, including the

Calvin cycle The Calvin cycle, light-independent reactions, bio synthetic phase, dark reactions, or photosynthetic carbon reduction (PCR) cycle of photosynthesis is a series of chemical reactions that convert carbon dioxide and hydrogen-carrier compounds into ...

in plants and

glycolysis Glycolysis is the metabolic pathway that converts glucose () into pyruvic acid, pyruvate and, in most organisms, occurs in the liquid part of cells (the cytosol). The Thermodynamic free energy, free energy released in this process is used to form ...

.Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. . It is the

phosphate ester In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered a ...

dihydroxyacetone Dihydroxyacetone (; DHA), also known as glycerone, is a simple saccharide (a triose) with formula . DHA is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, ...

Role in glycolysis

Dihydroxyacetone phosphate lies in the glycolysis metabolic pathway, and is one of the two products of breakdown of

fructose 1,6-bisphosphate Fructose 1,6-bisphosphate, known in older publications as Harden-Young ester, is fructose sugar phosphorylated on carbons 1 and 6 (i.e., is a fructosephosphate). The β-D-form of this compound is common in cells. Upon entering the cell, most glu ...

, along with

glyceraldehyde 3-phosphate Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GA3P, GADP, GAP, TP, GALP or PGAL, is a metabolite that occurs as an intermediate in several central pathways of all organisms.Nelson, D ...

. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate. ''The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.''

Role in other pathways

In the

, DHAP is one of the products of the sixfold reduction of

1,3-bisphosphoglycerate 1,3-Bisphosphoglyceric acid (1,3-Bisphosphoglycerate or 1,3BPG) is a 3-carbon organic molecule present in most, if not all, living organisms. It primarily exists as a metabolic intermediate in both glycolysis during respiration and the Calvin cycl ...

by NADPH. It is also used in the synthesis of sedoheptulose 1,7-bisphosphate and fructose 1,6-bisphosphate, both of which are used to reform

ribulose 5-phosphate Ribulose 5-phosphate is one of the end-products of the pentose phosphate pathway. It is also an intermediate in the Calvin cycle. It is formed by phosphogluconate dehydrogenase in the pentose phosphate pathway. Ribulose 5-phosphate is involved in ...

, the 'key' carbohydrate of the Calvin cycle. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate, which is part of the entry of

glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...

(sourced from

triglycerides A triglyceride (from ''wikt:tri-#Prefix, tri-'' and ''glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and oth ...

) into the

glycolytic pathway Glycolysis is the metabolic pathway that converts glucose () into pyruvate and, in most organisms, occurs in the liquid part of cells (the cytosol). The free energy released in this process is used to form the high-energy molecules adenosine trip ...

. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD⁺/NADH as cofactor. DHAP also has a role in the ether-lipid biosynthesis process in the protozoan parasite ''

Leishmania mexicana ''Leishmania mexicana'' is a species of obligate intracellular parasites of the protozoan genus ''Leishmania''. In Mexico and Central America, this parasite is the primary cause of cutaneous leishmaniasis. It is also endemic to Texas, where 69 ...

''. DHAP is a precursor to

2-oxopropanal Methylglyoxal (MGO) is the organic compound with the formula CH3C(O)CHO. It is a reduced derivative of pyruvic acid. It is a reactive compound that is implicated in the biology of diabetes. Methylglyoxal is produced industrially by degradation ...

. This conversion is the basis of a potential biotechnological route to the commodity chemical

1,2-propanediol Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An aliph ...

References

{{Glycolysis Photosynthesis Alpha-hydroxy ketones Organophosphates Phosphate esters Glycolysis Biomolecules Metabolic intermediates

Role in glycolysis

Role in other pathways

See also

References