| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - Synthesis and Biological Activity of N-Sulfonylphosphoramidates: Probing the Electrostatic Preferences of Alkaline Phosphatase
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - N-Sulfonylphosphoramidates have been synthesized to investigate the electrostatic requirementsfor binding to alkaline phosphatase. Alkyl- and aryl N-benzylated sulfonamides were phosphorylatedwith bromophosphates or synthesized via phosphoramidite chemistry in moderate yields (44−77%.)The resulting tribenzylated N-sulfonylphosphoramidates may be deprotected in one step to givethe free acids in quantitative yields. Physical data of N-sulfonylphosphoramidates, including pKa'sand stability toward hydrolysis, were determined. Inhibition data suggests that AP does not bindtrianionic N-sulfonylphosphoramidates better than dianionic N-sulfonylphosphoramidates, althoughN-sulfonylphosphoramidates are bound tighter than N-phenylphosphoramidate. kcat for thehydrolysis of N-sulfonylphosphoramidates by bovine and E. coli alkaline phosphatases is 10−60%that of p-nitrophenyl phosphate.
|
| article type
| |
| is part of this journal
| |
