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- W2076304316 abstract "(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 1 adopts a (4)C(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 (4)C(1) chair conformation. Surprisingly, compound 2 exhibits a different equilibrium between (1)C(4) chair and (1)S(3) skew boat conformations and significant flexibility around the pseudoglycosidic linkage when in solution. The beta-stereoisomer 3 adopts a major (4)C(1) chair conformation. Interestingly, C-galactosides 1, 2, and 3 bind to viscumin (VAA), a galactoside-specific lectin, which is confirmed by NMR experiments and docking calculations." @default.
- W2076304316 created "2016-06-24" @default.
- W2076304316 creator A5022208227 @default.
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- W2076304316 creator A5076231784 @default.
- W2076304316 creator A5082026323 @default.
- W2076304316 creator A5089398129 @default.
- W2076304316 date "2009-02-26" @default.
- W2076304316 modified "2023-10-11" @default.
- W2076304316 title "Synthesis and Conformational Analysis of (α‐<scp>D</scp>‐Galactosyl)phenylmethane and α‐,β‐Difluoromethane Analogues: Interactions with the Plant Lectin Viscumin" @default.
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- W2076304316 doi "https://doi.org/10.1002/chem.200801394" @default.
- W2076304316 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19185038" @default.
- W2076304316 hasPublicationYear "2009" @default.
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