Conformational flexibility of C-glycosides: Experimental evidence of the existence of a gauche-gauche conformation around the glycosidic linkage for a lactose analogue

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1467-1470

  Espinosa, Juan Félix ^a   Dietrich, Hansjörg ^a,b   Martín Lomas, Manuel ^a   Schmidt, Richard R ^b   Jiménez Barbero, Jesús ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE;

EID: 0029924495     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02397-6     Document Type: Article

References (15)

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3. Espinosa, J. F.; Martín-Pastor, M.; Asensio, J. L.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. Tetrahedron Lett. 1995, 36, 6329.
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9. Allinger, N. L.; Yuh, Y. H.; Lii, J. H. J. Am. Chem. Soc. 1989, 111, 8551.
10. Relaxed (Φ,Ψ) potential energy maps were calculated for 3 and 4 using MM3* (ε= 80) as integrated in MACROMODEL 4.5 (Mohamadi, F.; Richards, N. G. J.; Guida, W. C; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.) as described in Ref. 3. The three ideal staggered positions with respect to the Oα-Cα bond were also taken into account. In total, 9600 conformations were calculated.
11. C value of 0.17 ns.
12. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron, 1980, 36, 2783.
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14. Bernabé, M.; Fernandez-Mayoralas, A.; Jiménez-Barbero, J.; Martín-Lomas, M.; Rivera, A. J. Chem. Soc. Perkin Trans. 2, 1989, 1867.
15. Espinosa, J. F.; Cañada, F. J.; Asensio, J. L.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. Angew. Chem. Int. Ed. Engl., in the press.