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CHEMISTRY: WASHBURN AND READ
19'1
and into pyromucic acids under the same conditions as chondrosic acid, hence it was concluded that the two acids were similar in their structure, namely, that in both an oxygen bridge existed between the a- and al-carbon atoms.4 6. The anhydrodicarboxylic acids (derived from hexoseamines) have as many asymmetric carbon atoms in their molecule as the corresponding acids derived from hexoses. Therefore, there are possible only two optically inactive anhydrodicarboxylic acids: namely, one corresponding to mucic and the other to allomucc acid. This consideration limits the possibilities of configuration of epichondrosic acid to anhydromucic, or anhydroallomucic. The fact that chondrosamine forms a phenyl osazone identical in its properties with that of allose decides the choice between the two configurations in favor of anhydroallomucic. 7. Regarding the configuration of chondrosine the choice remains between that of l-allosamine or of l-altrosamine. Both anhydroallomucic and anhydrotalomucic acids are obtainable from chondrosamine depending on the procedure in preparation. It was attempted to prepare chondrosaminic acid synthetically from ribosimine by the action of prussic acid. The acid obtained in this manner had the composition of hexosaminic acid, C = 37.02%, H = 6.58%, and N = 7.44% (theory, C = 36.92, H = 6.66, N = 7.18). M. P. = 198°C., [a]" = - 9.4°. The acid was evidently epimeric with chondrosaminic, and on treatment with nitric acid it should have yielded chondrosic acid. Unfortunately for lack of material this experiment had to be deferred. 1 Fischer, E., and Leuchs, H., Berlin, Ber. D. chem. Ges., 36, 24 (1903). Irvine, J. C., and Hynd, A., London, J. Cemn. Soc., 101, 1128 (1912); 105, 698 (1914). 8 Levene, P. A., and La Forge, F. B., J. Biol. Chem., 18,123 (1914). 4 Fischer, E., and Tiemann, F., Berlin, Ber. D. chem. Ges., 24, 2139 (1