title: Complete NMR assignment and conformational analysis of 17-α-ethinylestradiol by using RDCs obtained in grafted graphene oxide.
abstract: The1H and13C NMR spectra of 17-α-ethinylestradiol (EE2), a well-known contraceptive, including diastereotopic methylene groups, were fully assigned with the help of residual dipolar couplings (RDC) measured in the recently developed grafted graphene oxide orienting medium. RDC analysis, which included all1DCHcouplings and the long-range2DCH1H-C≡13C coupling, also pointed to the presence of a minor conformation arising from pseudo-rotation of the steroid B ring. Saturation-transfer difference (STD) measurements revealed that the most likely interaction between EE2 and orienting medium occurred on the C and D ring. Copyright © 2016 John Wiley & Sons, Ltd.
authors.affiliation: Instituto Federal de Alagoas, Campus Piranhas, Avenida Sergipe, s/n° Xingó, 57460-000, Piranhas, AL, Brazil.
authors.forename: José A A
authors.initials: JA
authors.lastname: França
authors.affiliation: Departamento de Química Fundamental, Universidade Federal de Pernambuco, Avenida Professor Moraes Rego, 1235, Cidade Universitária, 50670-901, Recife, PE, Brazil.
authors.forename: Armando
authors.initials: A
authors.lastname: Navarro-Vázquez
authors.affiliation: School of Pharmaceutical Sciences, South Central University for Nationalities, Wuhan, 430074, PR China.
authors.forename: Xinxiang
authors.initials: X
authors.lastname: Lei
authors.affiliation: Leibniz-Institut für Molekulare Pharmakologie (FMP), Robert-Robert-Rössle-StraΒe 10, 13125, Berlin, Germany.
authors.forename: Han
authors.initials: H
authors.lastname: Sun
authors.affiliation: Department of NMR-based Structural Biology, Max Planck Institute for Biophysical Chemistry, Fassberg 11, 37077, Göttingen, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Griesinger
authors.affiliation: Departamento de Química Fundamental, Universidade Federal de Pernambuco, Avenida Professor Moraes Rego, 1235, Cidade Universitária, 50670-901, Recife, PE, Brazil.
authors.forename: Fernando
authors.initials: F
authors.lastname: Hallwass
mesh_terms: D002247:Carbon Isotopes / Q000737:chemistry; D004997:Ethinyl Estradiol / Q000737:chemistry*; D006108:Graphite / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008958:Models, Molecular; D008968:Molecular Conformation; D056004:Molecular Dynamics Simulation; D010087:Oxides / Q000737:chemistry*; D011522:Protons
chemical_list: D002247:Carbon Isotopes; D010087:Oxides; D011522:Protons; D004997:Ethinyl Estradiol; D006108:Graphite
keywords: 13C; 1H; NMR; STD; endocrine disruptors; ethinyl estradiol; grafted graphene oxide; molecular dynamics; prochiral assignment; residual dipolar couplings