Abstract
N.m.r. spectroscopy ( 1H- and 13C-) of N-glycolylneuraminic acid, and of its interaction product with Ca 2+ at pH 7, indicated that a 1:1 complex is formed, with a formation constant of 193 M −1 [compared to 121 M −1 for N-acetylneuraminic acid ( 1)]. From analysis of electric-field shifts, an approximate position of the Ca 2+ ion in the complex is inferred, with the hydroxyl group of the N-glycolyl group providing the additional binding. Compound 1 was oxidized with sodium periodate, and 13C-n.m.r. spectroscopy was applied in an attempt to identify the aldehyde formed, and to demonstrate that the loss of the glycerol-1-yl side-chain (carbon atoms 8 and 9) decreases its Ca 2+ ion-binding capacity.
Published Version
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