Synthesis of O-glycolyl-linked neuraminic acids through a spirocyclic intermediate.
[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.
McAuliffe
Joseph C
JC
The Burnham Institute, 10901 North Torrey Pines Road, San Diego, California 92037, USA.
Rabuka
David
D
Hindsgaul
Ole
O
D000818:Animals; D002236:Carbohydrate Conformation; D019281:Dimerization; D004187:Disaccharides / Q000138:chemical synthesis; D009438:Neuraminic Acids / Q000138:chemical synthesis*; D010063:Ovum / Q000737:chemistry; D012617:Sea Urchins / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry
D004187:Disaccharides; D009438:Neuraminic Acids; D013141:Spiro Compounds