The partitioning of phosphoramide mustard and its aziridinium ions among alkylation and PN bond hydrolysis reactions

EM Shulman-Roskes, DA Noe…

Index: Shulman-Roskes, Ellen M.; Noe, Dennis A.; Gamcsik, Michael P.; Marlow, Allison L.; Hilton, John; Hausheer, Frederick H.; Colvin, O. Michael; Ludeman, Susan M. Journal of Medicinal Chemistry, 1998 , vol. 41, # 4 p. 515 - 529

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Citation Number: 40

Abstract

NMR (1H and 31P) and HPLC techniques were used to study the partitioning of phosphoramide mustard (PM) and its aziridinium ions among alkylation and PN bond hydrolysis reactions as a function of the concentration and strength of added nucleophiles at 37° C and pH 7.4. With water as the nucleophile, bisalkylation accounted for only 10-13% of the product distribution given by PM. The remainder of the products resulted from PN bond ...