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Boletín de la Sociedad Chilena de Química
versão impressa ISSN 0366-1644
Resumo
COLMAN DE SAIZARBITORIA, T.; TILLETT, S. e MALAUGHLIN, J.L.. DETERMINATION ON THE ABSOLUTE CONFIGURATION OF XYLOPIACIN BY MOSHR ESTER METHODOLOGY AND MOLECULAR MODELING STUDIES. Bol. Soc. Chil. Quím. [online]. 2000, vol.45, n.4, pp.521-526. ISSN 0366-1644. http://dx.doi.org/10.4067/S0366-16442000000400002.
Xylopiacin 1, a cytotoxic mono-tetrahydrofuran Annonaceous acetogenin, hsa been isolated from the seeds of Xylopia aromatica (Lam.) Mart. (Annonaceae). The absolute configuration of this compound was determined by its Mosher ester derivatives. The sterogenic carbinol centers of xylopiacin S-MTPA 2 and xylopiacin R-MTPA 3 have been determined by 1H-NMR and 2D-NMR experiments utilizing Mosher esters. The preferred conformation of xylopiacin 1 and its derivatives 2 and 3 sere determined using molecular mechanics and molecular dynamics calculations
Palavras-chave : Acetogenins; absolute configuration; Mosher ester; molecular modeling.