Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 12, Pages 2861-2873Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801394
Keywords
carbohydrate mimics; lectin; molecular modeling; NMR spectroscopy; protein structures
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alpha-D-Galactosyl)phenylmethane (1). (alpha- and beta-D-galactosyl)-(difluoro)phenylmethane (2 and 3) have been prepared and their conformations in solution were described by using a combination of force-field calculations and NMR spectroscopic studies. Galactoside I adopts a C-4(1) chair conformation and an exo anomeric orientation. as is the case for natural alpha-galactosides. The X-ray crystal structure of its difluoromethylene derivative 2 similarly shows a C-4(1) chair conformation. Surprisingly, compound 2 exhibits a different equilibrium between C-1(4) chair and S-1(3) skew boat conformations and significant flexibility around the pseudoglycosidic linkage when in solution. The beta-stereoisomer 3 adopts a major C-4(1) chair conformation. Interestingly, C-galactosides 1, 2, and 3 bind to viscurnin (VAA), a galactoside-specific lectin, which is confirmed by NMR experiments and docking calculations.
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