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Synthesis of O-Glycolyl-Linked Neuraminic Acids through a Spirocyclic Intermediate

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journal contribution
posted on 16.08.2002, 00:00 by Joseph C. McAuliffe, David Rabuka, Ole Hindsgaul
The neuraminic acid derivative 5 is readily converted in several steps to the neuraminic acid dimer 12, linked through the hydroxyl of a 5-N-glycolyl group in an α-2,5 glycosidic linkage. The sequence is shown to proceed through a spirocyclic intermediate 9 by in situ NMR experiments. Similar derivatives of N-glycolylneuraminic acid (Neu5Gc), including polymers, have been identified from marine sources, including starfish and sea urchins, often as sulfated derivatives and are thought to mediate sperm−egg recognition.