Keto-eno tautomerization

Phosphorylation, reduction, and tautomerization. Reaction of 3-phos-phoglycerate with ATP generates the corresponding acyl phosphate, which is reduced by NADH/H to an aldehyde, Keto-eno] tautomerization of the aldehyde gives dihydroxyacetone phosphate, the same reaction as step 5 of glycolysis (Figure 29.4). 

The use of molecular models gained special prominence in the middle of the 19th century as the chemical significance of three-dimensional molecular shape became recognized [Brock, 2000]. While such structures could be represented on paper, physical models gave an immediacy and an ease of visualization that sketches alone did not provide. They also provided a framework in which certain theoretical concepts such as steric hindrance, tautomerism, conformational changes, and chirality could be explored. Famously, the discovery of the double helical structme of DNA was aided by the manipulation of physical models, specifically with respect to the keto/eno tautomerism of the bases [Watson, 1968],... 

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