Data di Pubblicazione:
2006
Citazione:
Synthesis and conformational analysis of galactose-derived bicyclic scaffolds / Silvia Mari, F. Javier Cañada, Jesús Jiménez-Barbero, Anna Bernardi, Gilles Marcou, Ilaria Motto, Ingrid Velter, Francesco Nicotra, Barbara La Ferla. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2006:13(2006), pp. 2925-2933. [10.1002/ejoc.200501012]
Abstract:
Two novel galactose-derived bicyclic acetamides were synthesized. The conformational behavior of these cyclic acetamides in aqueous solution was fully investigated. The NMR spectroscopic data suggests that the pyran ring interconverts between two (C-4(1), S-1(3)) or three (C-4(1), S-1(3) and C-1(4)) conformations and molecular modelling studies allowed the structures' geometries to be defined. Three different force fields were used (Amber*, MM3* and OPLSAA) and fitting procedures were employed to reproduce the experimental (3)J(H-H) coupling constants and NOE contacts. Evaluation of the results established which of these three well-known force fields were the most reliable in reproducing the experimental observations and should therefore be used for analogous design studies. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
NMR spectroscopy ; molecular modelling ; carbohydrates; carbohydrate mimics
Elenco autori:
S. Mari, F. Javier Cañada, Jesús Jiménez Barbero, A. Bernardi, M. Gilles, I.M. Motto, V. Ingrid, N. Francesco, Barbara La Ferla
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