Neuraminic Acid Derivatives Newly Discovered in Humans: N-Acetyl-9-O-L-lactoylneuraminic Acid, N,9-O-Diacetylneuraminic Acid and N-Acetyl-2,3-dehydro-2-deoxyneuraminic Acid

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Abstract
The free and glycosidically bound acylneuraminic acids from human serum and saliva and the free acylneuraminic acids from human urine were characterized by TLC and GLC/mass spectrometry. Acylneuraminic acid mixtures obtained from serum and saliva contain mainly N-acetylneuraminic acid and N-acetyl-9-O-L-lactoylneuraminic acid, whereas small amounts of N,9-O-diacetylneuraminic acid are also present. No free N,O-diacylneuraminic acids could be detected in the urine samples. None of the investigated fluids contained N-glycoloylneuraminic acid. The unsaturated N-acetyl-2,3-dehydro-2-deoxyneuraminic acid is usually a component of the free acylneuraminic acid fractions of serum, saliva and urine. The body fluids of a patient with sialuria contain the same O-acylated and unsaturated N-acetylneuraminic acid derivatives as mentioned above, but the total amounts of free acylneuraminic acids in these materials are significantly higher than found for normal persons.