O2-(N-hydroxy(methoxy)-2-ethanesulfonamido) protected diazen-1-ium-1,2-diolates: nitric oxide release via a base-induced β-elimination cleavage.

O(2)-(Ethanesulfohydroxamic acid) and O(2)-(N-methoxy-2-ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O(2)-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitric oxide release studies showed that O(2)-(N-methoxy-2-ethanesulfonylamido) diazeniumdiolates 5 and 7 released NO in a nonphysiological alkaline buffer, in the presence of bases such as the basic natural amino acids Arg and His, or the non-nucleophilic organic base DBU in PBS at pH 7.4, via a β-elimination cleavage reaction.