Glyceronic acid

Hexose diphosphate was found by Harden and Young69 in cell-free alcoholic-fermentation liquors. In 1930, it was observed that addition of fluoride to fermenting-yeast extracts leads to an accumulation of 0-phospho-D-glyceronic acid,60 which is also a metabolite of muscle extracts.61 Attention was turned, therefore, to the pathway from hexose diphosphate to 0-phos-pho-D-glyceronic acid. In 1932, Fischer and Baer62 described the synthesis of D-glycerose 3-phosphate, and, in 1933, Smythe and Gerischer63 noted... 

L-glyceronic acid. The formula XXXIV had also been proposed from the results of the application of the hydrazide rule28 to the hydrazide derivative of dihydrostreptosonic acid prepared by Folkers and coworkers.66... 

The action of ammonia on cytidine ribitol pyrophosphate (III) gave a cyclic phosphate IX which was oxidized by periodate and bromine to yield X, the cyclic 2,3-0-phosphate of glyceronic acid. This substance was purified by paper chromatography, and hydrolyzed with acid to the 2-phos-phate (XI) and 3-phosphate (XII) of D-glyceronic acid. These substances were utilized by a multi-enzyme system from rabbit muscle which degrades carbohydrates by way of the Embden-Meyerhof pathway. The ribitol phosphate (VII) is therefore L-ribitol 1-phosphate (o-ribitol 5-phosphate). ... 

The conversion, by bacterial extracts, of D-oZtro-heptulose 1,7-diphosphate to shikimate, essentially without side reactions, greatly facilitated subsequent study of the intermediate steps in the synthesis. It was shown that the addition of iodoacetate or fluoride completely blocks this conversion. In the presence of iodoacetate, synthesis is restored by the addition of either D-glyceronic acid 3-phosphate or enolpyruvate phosphate. In the presence of fluoride, only enolpyruvate phosphate is able to restore shikimate synthesis. Neither D-fructose 1,6-diphosphate nor pyruvate reverses these inhibitions. These results suggested that the reactions of glycolysis, from triose phosphate to enolpyruvate phosphate (see Fig. 2), are involved in the conversion of D-oZfro-heptulose diphosphate to shikimate. The effect... 

Sucrose was oxidized by Fleury and Courtois, who obtained a tetra-aldehyde (87) which was oxidized by bromine, in the presence of strontium or barium carbonate, to the corresponding tetracarboxylic acid salt the latter compound was hydrolyzed with acid to yield D-glyceronic acid, glyoxylic acid, and hydroxypyruvic acid, which spontaneously decomposed into carbon dioxide and glycolaldehyde. It was found that oxysucrose shows four aldehyde groups from hypoiodite estimation, but only two from mercurimetry the latter result was attributed to steric hindrance, but it would seem more likely that, under the conditions of the determination. 

Oxyamygdalin has been prepared and further oxidized to the tetracar-boxylic acid, which gave mandelic, glyoxylic, and glyceronic acids on hydrolysis."... 

Methyl-D-glyceronic acid 2-Methyl-n-glyceronic acid 2-Deoxy-2- (hydroxy-methyl)glyceronic acid 3-hydroxy-2- (hydroxy-methyl)propanoic acid... 

A last attempt at synthesis was made by the preparation of 2-(hydroxy-methyl)glyceronic acid from 1,3-dihydroxy-2-propanone, but this product has not to date been transformed into the desired saccharinic acid (VI). Thus, this optically inactive acid has not been obtained in definitive form, nor have any of its derivatives been reported in the literature. 

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