Org Lett 2002 Sep 05;418:3067-9. doi: 10.1021/ol026317g.

Synthesis of O-glycolyl-linked neuraminic acids through a spirocyclic intermediate.

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[reaction: see text] 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 alpha-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.

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Genes referenced: LOC100887844 LOC100893217