Abstract
This article presents a new synthetic method for the preparation of cytidine-5′-monophospho-neuraminic acid analogues (CMP-NeuAc analogues) and the application of this reaction in combination with sialyltransferases. Several CMP-NeuAc analogues have been synthesized in moderate yields. The sialyltransferase reaction has further been applied to glycoprotein immobilization, in which a CMP-NeuAc was attached to a solid support at the 9″ position and the ability of this imbobilized molecule to effect a transfer reaction was confirmed by an assay using an asialoglycoprotein as the acceptor. Another aspect is a chemoenzymatic synthesis of modified sialyloligosaccharide. 9-Deoxy-9-fluoro- [3-13C] -NeuAc-α-2, 6- [U-13C] -Gal-β-1, 4-GlcNAc sequence was synthesized at the nonreducing end of an intact glycoprotein (ovalbumin) and its conformational properties were analyzed by NMR spectroscopy. The conformational properties of sialylgalactoside on this protein turned out to be similar to those of NeuAc-α-2, 6-Gal-β-1, 4-GlcNAc-β-1- O (CH2) 8COOMe.
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