This hot article from Julio Casado and colleagues at the University of Salamanca provides the first study of the alkylating ability of p-nitrostyrene oxide (pNSO), which is widely used in the pharmaceutical industry as a chiral building block for a variety of drugs. pNSO is also used as a substrate to study the activity of epoxide hydrolases and in polymer production.
4-(p-nitrobenzyl)pyridine (NBP), a model nucleophile for DNA bases, was used to study the alkylating effects of pNSO. They found that although pNSO is a strong alkylating agent, it has low efficacy – probably due to the instability of the NBP-pNSO adduct formed. A previously unreported pNSO-guanosine adduct was also detected.
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Reactivity of p-nitrostyrene oxide as an alkylating agent. A kinetic approach to biomimetic conditions
Marina González-Pérez, Rafael Gómez-Bombarelli, M. Teresa Pérez-Prior, José A. Manso, Isaac F. Céspedes-Camacho, Emilio Calle and Julio Casado
Org. Biomol. Chem., 2011, Advance Article