Synthesis of an Affinity Adsorbent for Sialidase

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Abstract
The reaction of the sodium salt of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacro-2-nonulopyranosonate (1) with styrene oxide, followed by deprotection, gave the diastereomeric mixture of (β-hydroxyphenethyl) 5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galycto-2-nonulopyranosidoic acid (3). The thioglycoside 3 was proved to be an inhibitor for Clostridium perfringens sialidase. An affinity adsorbent with immobilized sialic acid through a thioglycosidic linkage was prepared by treatment of 1 with epoxy-activated Sepharose 4B. The synthetic adsorbent was proved to adsorb Cl. perfringens sialidase specifically and to be capable of repeated operation.