2 — ketogluconic acid

Ketogluconic acid Pseudomonas sp. Intermediate for D-araboascorbic acid... 

Fumaric acid Itaconic acid Citric acid Kojic acid 2-Ketogluconic acid 5-Ketogluconic acid Gluconic acid Mannitol ... 

Duff, R. B., Webley, D. M. Scott, R. O. (1963). Solubilization of minerals and related materials by 2-ketogluconic acid-producing bacteria. Soil Science, 95, 105-14. 

G. B. Paerels, Crystalline 3-desoxy-2-ketogluconic acid, Rec. Trav. Chim. (Pays-Bas), 80 (1961) 985-988. 

Fig. 8.12 Microbial production routes to 3-hydroxypropanoic acid. Compounds 3HPCoA, 3-hydroxypropanoyl coenzyme A ester 2KGA, 2-ketogluconic acid MSA, malonate semialdehyde. Enzymatic activities AAM, alanine-2,3-aminomutase TA, transaminase.

Ketogluconic acid + H2O2 Glucosone Glucose-1 -oxidase... 

Duff, R.B., and Webley, D.M., 1959. 2-ketogluconic acid as a natural chelator produced by soil bacteria. Chem. Ind., 1376—1377. 

Webley, D.M. and Duff, R.B., 1965. The incidence, in soils and other habitats, of microorganisms producing 2-ketogluconic acid. Plant Soil, 22 307—313. 

Serratia marcescens Collagen membrane Glucose 2-Ketogluconic acid... 

G, and Naresh Kumar, G. (2013) 2-Ketogluconic acid secretion by incorporation of Pseudomonas putida KT 2440 gluconate dehydrogenase (gad) operon in Enterobacter asburiae PSI3 improves mineral phosphate solubilization. Curr. Microbiol, 67 (3), 388-394. 

Ketogluconic acid. 2-Oxoglucordc acid. Fructurortic acid. 2-Ketomannonic acid. Glucosortic acid... 

Ketogluconic acid has been isolated from a polysaccharide occurring in Irish moss 119), but no other similar product has been found in nature. Both 2-keto- and 5-ketogluconic acids have been prepared by the action of bacteria. Pyruvic acid and a-ketoglutaric acid (Chapter XIII) are also keto acids. 

The similarity of the keto aldonic acids and uronic acids has been mentioned earlier. 2-Ketogluconic acid gives a 33 % yield of furfural in 4 hours and the 5-keto acid 42.5%, when heated with 12% hydrochloric acid ISO), The evolution of carbon dioxide from the 5-keto acid is quantitative. 

Ketogluconic acid and its lactone exist only as sirups although hygroscopic crystals of the former have been reported 124)- Esters can be easily prepared by the action of methanol and sulfuric acid on the sodium salt 122,132). The ester and salt mutarotate in the same direction as fructose. Ultraviolet absorption spectra 133) of solutions of the salts and acid indicate the absence of carbonyl or carboxyl groups, and, for alkaline solutions, the absorption is typical of an ethylenic or enolic linkage. 

A 3-deoxy-2-ketogluconic acid 6-phosphate was isolated as an intermediate in the enzymic oxidation of gluconic acid 6-phosphate 135a). The formation of this acid by a dehydration mechanism is reminiscent of that of the saccharinic acids. 

Substituted osones can be synthesized by the Grignard reaction. Di-0-isopropylidene-2-ketogluconic acid and phenyl magnesium bromide react to form l-C-phenyl-2,3,4,5-di-0-isopropylideneglucosone Some 1,1-C-diphenyl-2,3,4,5-di-0-isopropylidenefructose is also formed. Hydrolysis with boiling normal sulfuric acid in propanol forms the 1-C-phenylgluco-sone. This product is the first osone prepared in crystalline form. 

More drastic oxidation of aldoses with hypoiodite leads to keto acids and finally to cleavage of carbon-carbon bonds. Honig and Tempus 199) claimed to have oxidized glucose stepwise to gluconic acid, 2-ketogluconic acid, and n-arabonic acid. However, other workers claim that the main product is 5-ketogluconic acid 200),... 

The nature of the products formed under various conditions and the mechanism of the reaction have been investigated by Kiichlin 252). At low temperatures and for dilute solutions in the presence of ferrous sulfate, the following products were formed from glucose and identified as derivatives glucosone, 2-ketogluconic acid, and 2,3-diketogluconic acid in concentrated solutions, formaldehyde also was found. The formation of these products at low temperatures was ascribed to the following series of reactions ... 

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