N-Arabonic acid

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),... 

D-Gluconic acid, ammonium n-gluconate, sodium n-gluconate D-Arabonic acid, L-arabonic acid, potassium n-arabonate, citric acid D-Mannonic acid a-n-Galacturonic acid... 

The aldonic acids of the pentose series were prepared similarly. L-Arabonic acid was isolated by Kiliani as the calcium salt, and Ruff prepared calcium n-arabonate. In the latter case almost quantitative yields were reported. n-Lyxonic acid was isolated as the basic lead salt and converted to the crystalline lactone by Wohl and List. n-Ribose was oxidized to the crystalline cadmium n-ribonate by Levene and Jacobs the yield was less than 50%. The well-known boat-shaped crystals of the double salt of cadmium n-xylonate-cadmium bromide were prepared by the oxidation of n-xylose with an excess of bromine by Ruff, followed by a subsequent treatment with cadmium carbonate. Ruff also prepared L-erythronic acid, isolating it as the brucine salt the starting material was a crude n-erythrose sirup prepared by degradation of calcium L-arabonate. 

Certain bacteria of the acetic acid group have been reported to produce D-arabonic acid from n-arabinose, and indeed pentonic acids from xylose... 

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