A direct HPLC enantioseparation of three representative compounds of a new family of potential non-peptide beta-secretase inhibitors was performed on the immobilized Chiralpak IA chiral stationary phase. Semipreparative amounts of enantiopure forms were collected and submitted to stereochemical characterization. The absolute configuration was assigned by a multi-step methodology based on the combination of Masher's method with circular dichroism (CD) spectroscopy. The results from the NMR/CD study fully correlated the configurational assignment obtained by a second approach involving single crystal X-ray diffraction. (C) 2010 Elsevier B.V. All rights reserved.
Enantioselective HPLC combined with spectroscopic methods: A valid strategy to determine the absolute configuration of potential beta-secretase inhibitors / R., Cirilli; R., Ferretti; LA REGINA, Giuseppe; G., Morelli; Pierini, Marco; Piscitelli, Francesco; Silvestri, Romano. - In: TALANTA. - ISSN 0039-9140. - 82:4(2010), pp. 1306-1312. [10.1016/j.talanta.2010.06.060]
Enantioselective HPLC combined with spectroscopic methods: A valid strategy to determine the absolute configuration of potential beta-secretase inhibitors
LA REGINA, GIUSEPPE;PIERINI, MARCO;PISCITELLI, FRANCESCO;SILVESTRI, Romano
2010
Abstract
A direct HPLC enantioseparation of three representative compounds of a new family of potential non-peptide beta-secretase inhibitors was performed on the immobilized Chiralpak IA chiral stationary phase. Semipreparative amounts of enantiopure forms were collected and submitted to stereochemical characterization. The absolute configuration was assigned by a multi-step methodology based on the combination of Masher's method with circular dichroism (CD) spectroscopy. The results from the NMR/CD study fully correlated the configurational assignment obtained by a second approach involving single crystal X-ray diffraction. (C) 2010 Elsevier B.V. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
