Experimental and theoretical evidences of conformational flexibility of C-glycosides. NMR analysis and molecular mechanics calculations of C-lactose and its O-analogue

doi:10.1016/0040-4039(95)01223-5

Tetrahedron Letters

Volume 36, Issue 35, 28 August 1995, Pages 6329-6332

https://doi.org/10.1016/0040-4039(95)01223-5 Get rights and content

Abstract

NMR data (NOEs and coupling constants) and MM3^∗ molecular mechanics calculations have allowed to demonstrate that the conformational behaviour of C-lactose is different of its O-analogue. The glycosidic linkages, particularly the C-aglyconic bond, present a high degree of flexibility and, therefore, the conformational entropy of C-lactose is higher than that of its O-counterpart.

NMR data (NOEs and coupling constants) and MM3^∗ molecular mechanics calculations have allowed to demonstrate that the conformational behaviour of C-lactose is different of its O-analogue.

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Experimental and theoretical evidences of conformational flexibility of C-glycosides. NMR analysis and molecular mechanics calculations of C-lactose and its O-analogue

Abstract

Curr. Opinion Struct. Biol.

Curr. Opinion Struct. Biol.

Carbohydr. Res.

Carbohydr. Res.

Science

Carbohydr. Lett.

Liebigs Ann. Chem.

J. Org. Chem.

J. Org. Chem.

Biochem. Soc. Trans.