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Dihydroxyacetone (/ ˌ d aɪ h aɪ ˌ d r ɒ k s i ˈ æ s ɪ t oʊ n / ⓘ; DHA), also known as glycerone, is a simple saccharide (a triose) with formula C 3 H 6 O 3. 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, and by the fermentation of glycerin.
Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH 2 C(O)CH 2 OPO 3 2-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis. [1] [2] It is the phosphate ester of dihydroxyacetone.
[1] [2] The simplest ketose is dihydroxyacetone ((CH 2 OH) 2 C=O), which has only three carbon atoms. It is the only ketose with no optical activity . All monosaccharide ketoses are reducing sugars , because they can tautomerize into aldoses via an enediol intermediate, and the resulting aldehyde group can be oxidised , for example in the ...
An oligosaccharide has both a reducing and a non-reducing end. The reducing end of an oligosaccharide is the monosaccharide residue with hemiacetal functionality, thereby capable of reducing the Tollens’ reagent, while the non-reducing end is the monosaccharide residue in acetal form, thus incapable of reducing the Tollens’ reagent. [2]
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.
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Glycerol-3-phosphate dehydrogenase (GPDH) is an enzyme that catalyzes the reversible redox conversion of dihydroxyacetone phosphate (a.k.a. glycerone phosphate, outdated) to sn-glycerol 3-phosphate. [2] Glycerol-3-phosphate dehydrogenase serves as a major link between carbohydrate metabolism and lipid metabolism.
The structure of TPI facilitates the conversion between dihydroxyacetone phosphate (DHAP) and glyceraldehyde 3-phosphate (GAP). The nucleophilic glutamate 165 residue of TPI deprotonates the substrate , [ 4 ] and the electrophilic histidine 95 residue donates a proton to form the enediol intermediate.