Synthesis of sialyl Lewis x mimetics as selectin inhibitors by enzymatic aldol condensation reactions.
Several D-mannosyl phosphate/phosphonate derivatives have been enzymatically prepared as sialyl Lewis x tetrasaccharide mimics, which showed strong-to-moderate inhibition against E-, P-, and L-selectins. The synthesis of these mimics is very straightforward; mannosyl aldehyde derivatives are condensed with dihydroxyacetone phosphate (DHAP) in the presence of a DHAP-dependent aldolase to provide mannosyl phosphates.
Lin
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Department of Chemistry and Skaggs Institute of Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA.
Morís-Varas
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Weitz-Schmidt
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Wong
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D002236:Carbohydrate Conformation; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry* / Q000494:pharmacology; D019087:Selectins / Q000187:drug effects*; D000080506:Sialyl Lewis X Antigen
D009844:Oligosaccharides; D019087:Selectins; D000080506:Sialyl Lewis X Antigen; D005634:Fructose-Bisphosphate Aldolase