Gomes, PGomes, JRBRodrigues, MMoreira, R2015-12-302015-12-302003TETRAHEDRON. - Vol. 59, n. 38 (SEP 15 2003), p. 7473-74800040-4020http://hdl.handle.net/10451/21512Acylation of antimalarial and bacteriostatic sulfonamides with N-protected amino acids and peptides was carried out using standard peptide coupling methods. These acylation reactions are regioselective for the N-4 nitrogen atom of diazine-containing sulfonamides. In contrast, only N-1 coupling was found for sulfisoxazole, an isoxazole-based sulfonamide. Computational studies suggest that a combination of geometrical, thermodynamic and electronic factors are responsible for the different reactivities reported. (C) 2003 Elsevier Ltd. All rights reserved.application/pdfengChemistry, Organicjournal articlehttp://dx.doi.org/10.1016/S0040-4020(03)01206-7