Optically active cyclophane receptors for mono??and disaccharides: The role of bidentate ionic hydrogen bonding in carbohydrate recognition

AS Droz, U Neidlein, S Anderson, P Seiler…

Index: Droz, Anne Sophie; Neidlein, Ulf; Anderson, Sally; Seiler, Paul; Diederich, Francois Helvetica Chimica Acta, 2001 , vol. 84, # 8 p. 2243 - 2289

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Citation Number: 80

Abstract

Abstract A new family of optically active cyclophane receptors for the complexation of mono- and disaccharides in competitive protic solvent mixtures is described. Macrocycles (−)-(R, R, R, R)-1–4 feature preorganized binding cavities formed by four 1, 1′-binaphthalene-2, 2′- diyl phosphate moieties bridged in the 3, 3′-positions by acetylenic or phenylacetylenic spacers. The four phosphodiester groups converge towards the binding cavity and ...