Abstract
Several phosphoramidate analogues of CMP-N-acetylneuraminic acid were prepared for evaluation as inhibitors of alpha-2,3- and alpha-2,6-sialyltransferase. Central to the synthesis was the oxidative coupling of an amino acid ester with an H-phosphonate to construct the phosphoramidate linkage. All compounds synthesized were weak inhibitors of both of the sialyltransferases as determined by an HPLC-based inhibition assay.
Publication types
-
Research Support, Non-U.S. Gov't
-
Research Support, U.S. Gov't, Non-P.H.S.
-
Research Support, U.S. Gov't, P.H.S.
MeSH terms
-
Carbohydrate Sequence
-
Chromatography, High Pressure Liquid
-
Cytidine Monophosphate / analogs & derivatives*
-
Cytidine Monophosphate / chemical synthesis
-
Cytidine Monophosphate / pharmacology
-
Drug Design
-
Enzyme Inhibitors / chemical synthesis*
-
Enzyme Inhibitors / pharmacology*
-
Kinetics
-
Molecular Sequence Data
-
Sialyltransferases / antagonists & inhibitors*
-
Spectrophotometry, Ultraviolet
Substances
-
Enzyme Inhibitors
-
Sialyltransferases
-
Cytidine Monophosphate