D-Glucosaminic acid

Let us now return to the pioneering work of Fischer and Tiemann.4 Chitonic acid is produced from D-glucosamine by deamination and oxidation, in that order. If the order is reversed, however, i. e., if D-glucos-amine is first oxidized to D-glucosaminic acid (2-amino-D-gIuconic acid) and the latter substance subsequently deaminated, chitonic acid is not the product. Instead an isomeric 2,5-anhydro hexonic acid (chitaric acid) is obtained. These facts may be summarized thus ... 

Further consideration needs to be given to the interesting fact that although D-glucosaminic acid (2-amino-D-gluconic acid) undergoes de-amination. with the establishment of a 2,5-anhydro ring, the deamination... 

Pezzotti, F., Therisod, H. and Therisod, M., Enz3Tnatic synthesis of D-glucosaminic acid from D-glucosamine. Carbohydr. Res., 2005, 340, 139. 

Hope, D.B. and Kent, P.W., Ester and lactone linkages in acidic polysaccharides. Part II. Lactones of D-glucosaminic acid. J. Chem. Soc. Abstr., 1955, 1831. 

J. M. Merrick and S. Roseman, D-Glucosaminic acid dehydrase, Methods Enzymol., 9 (1966) 657-660. 

Crystalline benzimidazoles have been obtained from all aldonic acids so far tested with only one exception that is known to the writer. Lohmar and Link29 reported that the condensation of D-glucosaminic acid (= 2-amino-2-desoxy-D-gIuconic acid) with o-phenylenediamine under a variety of conditions failed to yield a crystalline product. The direct oxidative condensation of D-glucosamine hydrochloride with o-phenylenediamine in the presence of cupric acetate yielded only the known 2-(D-arofro-tetrahydroxybutyl)quinoxaline (III) and not the desired benzimidazole. 

D-Glucosaminic acid (2-Amino-2-deoxy-D-gluconic acid)... 

Figure 5.16 The final products of hyaiuronan oxidative destruction,(A) 4,5 unsaturated ClcUA(d1-3)ClcNAc(bi-3)-D-pentauronic acid (B) 4,5 unsaturated Glc UA(bl-3)-N-acethyl-D- glucosamine acid (C) L-tri-tetradialdocyl-(bi-3)ClcNAc...

Desoxy-D-glucosaminic acid y-lactone hydrochloride dissolved in 15%-excess N NaOH, heated a few hrs. at 70-90°, cooled to 0°, neutralized with N HCl, Ag- or Na-nitrite added, more N HCl added during 4 hrs. at 0° with moderate vibration until after ca. 1 hr. Kl-starch-paper gives a positive reaction and pH 1 is reached, allowed to warm to 20° and stirred 30 hrs. 3-desoxy-D-chitaric acid. Y 61-80%. E. Hardegger, H. Furter, and J. Kiss, Helv. 41, 2401 (1958). 

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