5- Deoxypentonic acid

It should be noted that this assignment of configuration to the 3-deoxypentonic acids, taken in conjunction with the evidence cited in the preceding Section, also confirms the d configuration for the penultimate, secondary carbon atom of a -D-isosaccharinic acid. 

The directions of the optical rotations of the lactones (presumably gamma lactones) and phenylhydrazides of the four 3-deoxypentonic acids are in agreement with those predicted, on the basis of the assigned configurations, by the lactone and phenylhydrazide rules. 

Deoxypentonic acid y-lactone, 9CI. 2-Hydroxy-4-hydroxymethyl-4-butanolide [74243-47-3]... 

D-fzraZ>mo-hexos-2-ulose additionally underwent elimination of glucose to give an unstable 1,2,3-tricarbonyl intermediate which led to either 3,4-dihydroxy butanoic acid or 3-deoxypentonic acids it was concluded that the formation of aldonic acid end groups via terminal aldosuloses is unimportant in the oxygen-hydrogen carbonate treatment of (1 4) linked polysac-... 

Unlike 2-deoxyaldonic acids the 3-deoxy analogues can lose the ester function by cleavage of the Ci-C2 bond to give M-117 (e.g. m/z 117 in lactic acid, m/z 219 in 3-deoxytetronic acid (Fig. 5.15) and related ions [e.g. m/z 231 in 3-deoxypentonic acids (M-117 90)]. 

Ammo-l-(2-deoxy-erythro -pentofuranosyl)purine, D-338 2-Ammo-9-(2-deoxy-erythro -pentofuranosyl)-6-purinone, D-360 2-Amino-2-deoxypentonic acid, A-469... 

A marked difference in the product pattern has been reported for the treatment of cellobiose with either NaOH or NaHCOs. The formation of 3-deoxy-2-0-(hydroxymethyl)pentonic acids (52) from cellobiose is less important in sodium hydrogencarbonate solution than in sodium hydroxide, while the relative amounts of 2-deoxytetronic, 3-deoxypentonic, and 3,4-dideoxypentonic acids are much larger. 

Fig. 11.10 Chromatogram of organic acids extracted using DEAE-Sephadex from the urine of the same patient described in the legend to Fig. 11.9, after 1 year on vitamin B12 therapy. Separated as described for Fig. 11.9. Peak identifications are given in the legend to Fig. 11.9, additional identifications are 10, 2-deoxytetronate 17,4-hydroxyphenyl-acetate 18, 2-deoxypentonate. The reduced excretion of methylmalonate and the abolition of methylcitrate and 3-hydroxypropionate excretion together with the production of an otherwise normal urinary organic acid profile is apparent when compared to Fig. 11.9. (The horizontal axis represents the time elapsed in minutes from sample injection.) (Redrawn from the original, after Chalmers, 1980)...

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