4,8-anhydro-N-acetylneuraminic acid. Isolation from edible bird's nest and structure determination

A new, sialic-acid-derived compound was isolated from the acid hydrolysate of edible bird's nest by ion-exchange chromatography. Combined use of mass spectroscopy and 1H- and 13C-NMR spectroscopy established that it is the 4,8-anhydro derivative of N-acetylneuraminic acid and that in solutions it exists in two tautomeric forms. The formation of the new compound supports and earlier findings that in the glycoprotein of edible bird's nest at least a portion of N-acetylneuraminic acid is acetylated at HO-4.