Untersuchungen über die Konstitution der Neuraminsäure

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Abstract
The authors base their work on an empirical formula of neuraminic acid of C10H19O9 N. There is still considerable controversy on this, as Gottschalk has recently proposed a structure based on the empirical formula C9H17O8N. The substance contains a carboxyl group and a primary amino group. The reaction of periodate with neuraminic acid methyl glycoside was studied. The oxidation of N-acetyl-neuraminic acid according to Willstatter-Studel is described; this was followed by reduction with HI and red P. Two ninhydrin-positive spots were obtained, which have not yet been identified. Reaction of the methyl glycoside with HBr led in good yield to an unidentified crystalline product which has the same empirical formula as neuraminic acid, but no longer reacts with methanolic HCl; it is thus not neuraminic acid. It is non-reducing. Several infrared spectra are given. On the basis of these and previous results the currently proposed structures of neuraminic acid are criticized and a new one is proposed.