4388-26-5Relevant academic research and scientific papers
Synthesis and biological activity of N-sulfonylphosphoramidates: Probing the electrostatic preferences of alkaline phosphatase
Burlingham,Widlanski
, p. 7561 - 7567 (2007/10/03)
N-Sulfonylphosphoramidates have been synthesized to investigate the electrostatic requirements for binding to alkaline phosphatase. Alkyl- and aryl N-benzylated sulfonamides were phosphorylated with bromophosphates or synthesized via phosphoramidite chemistry in moderate yields (44-77%.) The resulting tribenzylated N-sulfonylphosphoramidates may be deprotected in one step to give the free acids in quantitative yields. Physical data of N-sulfonylphosphoramidates, including pKa's and stability toward hydrolysis, were determined. Inhibition data suggests that AP does not bind trianionic N-sulfonylphosphoramidates better than dianionic N-sulfonylphosphoramidates, although N-sulfonylphosphoramidates are bound tighter than N-phenylphosphoramidate. kcat for the hydrolysis of N-sulfonylphosphoramidates by bovine and E. coli alkaline phosphatases is 10-60% that of p-nitrophenyl phosphate.
