Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases.
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.
Whalen
Lisa J
LJ
University of Colorado, Department of Chemistry and Biochemistry, UCB 215, Boulder, CO 80309-0215, USA.
McEvoy
Kerry A
KA
Halcomb
Randall L
RL
D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D003568:Cytidine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D007700:Kinetics; D008969:Molecular Sequence Data; D012799:Sialyltransferases / Q000037:antagonists & inhibitors*; D013056:Spectrophotometry, Ultraviolet
D004791:Enzyme Inhibitors; D012799:Sialyltransferases; D003568:Cytidine Monophosphate