| Abstract
| - This paper describes the synthesis of 1,1-linked galactosyl mannosides as sialyl Lewis X mimeticsthat contain a spiro-ring to position the carboxylate group in a well-defined orientation. It wasfound that compound 4 is more active as a P-selectin inhibitor (IC50 = 19 μM) than the parentdisaccharide 2, which contains a flexible carboxyl group (IC50 = 193 μM). This result is consistentwith that observed in the previous NMR study of sialyl Lewis X bound to P-selectin. The chemistrydescribed here should be useful for the development of selective inhibitors of E-, P-, and L-selectins.
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