title: Synthesis of sialyl Lewis x mimetics as selectin inhibitors by enzymatic aldol condensation reactions.
abstract: 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.
authors.affiliation: Department of Chemistry and Skaggs Institute of Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA.
authors.forename: C C
authors.initials: CC
authors.lastname: Lin
authors.forename: F
authors.initials: F
authors.lastname: Morís-Varas
authors.forename: G
authors.initials: G
authors.lastname: Weitz-Schmidt
authors.forename: C H
authors.initials: CH
authors.lastname: Wong
mesh_terms: 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
chemical_list: D009844:Oligosaccharides; D019087:Selectins; D000080506:Sialyl Lewis X Antigen; D005634:Fructose-Bisphosphate Aldolase