Conformational Behavior of Aza-C-Glycosides: Experimental Demonstration of the Relative Role of the exo-anomeric Effect and 1,3-Type Interactions in Controlling the Conformation of Regul
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- 作者：Juan Luis Asensio ; F. Javier Cañ ; ada ; Alicia Garcí ; a-Herrero ; Marí ; a T. Murillo ; Alfonso Ferná ; ndez-Mayoralas ; Brian A. Johns ; Janusz Kozak ; Zhenzyu Zhu ; Carl R. Johnson ; and J
- 刊名：Journal of the American Chemical Society
- 出版年：1999
- 出版时间：December 15, 1999
- 年：1999
- 卷：121
- 期：49
- 页码：11318 - 11329
- 全文大小：462K
- 年卷期：v.121,no.49(December 15, 1999)
- ISSN：1520-5126
文摘
The conformational behavior of different aza-C-glycosides synthesized as glycosidase inhibitorshas been studied using a combination of NMR spectroscopy (J and NOE data) and time-averaged restrainedmolecular dynamics calculations. The obtained results show that the population distribution of conformersaround their pseudoglycosidic linkages is mainly controlled by 1,3-syn-diaxial interactions. Electrostatic effectsslightly modulate the conformational equilibrium. This result is in contrast with that observed for O-glycosides.For these natural compounds, the conformational behavior around the glycosidic linkage 
is mainly governedby the exo-anomeric effect. Experimentally based energy values for both the 1,3-syn-diaxial interactions andthe stereoelectronic effect have been deduced. Finally, the inhibitory activity of these compounds has beentested again a variety of glycosidase enzymes.
is mainly governedby the exo-anomeric effect. Experimentally based energy values for both the 1,3-syn-diaxial interactions andthe stereoelectronic effect have been deduced. Finally, the inhibitory activity of these compounds has beentested again a variety of glycosidase enzymes.