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Structural Relationship between Sialic Acid, Neuraminic Acid and 2-Carboxy-Pyrrole

Abstract

AN interesting field of biochemical research was opened when Blix1 isolated from bovine submaxillary gland mucin a crystalline reducing acid, named sialic acid2. Its most probable composition is given as C13H23NO11 or C13H21NO10.H2O. Bovine sialic acid contains an N-acetyl and an O-acetyl group, one primary alcohol group and a total of five hydroxyl groups3. Consumption of free iodine, when sialic acid is titrated with hypoiodite, and of one molecule of hydrogen, when the acid is submitted to treatment with sodium borohydride, is interpreted by Blix et al. 3 as indicating the presence of a free aldehyde group. The liberation of less than one mole carbon monoxide per mole sialic acid upon treatment with sulphuric acid would suggest the presence of an α-hydroxy group3.

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GOTTSCHALK, A. Structural Relationship between Sialic Acid, Neuraminic Acid and 2-Carboxy-Pyrrole. Nature 176, 881–882 (1955). https://doi.org/10.1038/176881a0

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