title: Iterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose.
abstract: The ab initio design of synthetic molecular receptors for a specific biomolecular guest remains an elusive objective, particularly for targets such as monosaccharides, which have very close structural analogues. Here we report a powerful approach to produce receptors with very high selectivity for specific monosaccharides and, as a demonstration, we develop a foldamer that selectively encapsulates fructose. The approach uses an iterative design process that exploits the modular structure of folded synthetic oligomer sequences in conjunction with molecular modelling and structural characterization to inform subsequent refinements. Starting from a first-principles design taking size, shape and hydrogen-bonding ability into account and using the high predictability of aromatic oligoamide foldamer conformations and their propensity to crystallize, a sequence that binds to β-D-fructopyranose in organic solvents with atomic-scale complementarity was obtained in just a few iterative modifications. This scheme, which mimics the adaptable construction of biopolymers from a limited number of monomer units, provides a general protocol for the development of selective receptors.
authors: 1] University of Bordeaux, CBMN (UMR 5248), Institut Européen de Chimie et Biologie, 2 rue Escarpit, Pessac 33600, France [2] CNRS, CBMN (UMR 5248), France.
authors: Nagula
authors: N
authors: Chandramouli
authors: 1] University of Bordeaux, CBMN (UMR 5248), Institut Européen de Chimie et Biologie, 2 rue Escarpit, Pessac 33600, France [2] CNRS, CBMN (UMR 5248), France.
authors: Yann
authors: Y
authors: Ferrand
authors: 1] University of Bordeaux, CBMN (UMR 5248), Institut Européen de Chimie et Biologie, 2 rue Escarpit, Pessac 33600, France [2] CNRS, CBMN (UMR 5248), France.
authors: Guillaume
authors: G
authors: Lautrette
authors: 1] University of Bordeaux, IECB (UMS 3033), Institut Européen de Chimie et Biologie, 2 rue Escarpit, Pessac 33600, France [2] CNRS, IECB (UMS 3033), France [3] INSERM, IECB (US 001), France.
authors: Brice
authors: B
authors: Kauffmann
authors: 1] University of Bordeaux, ARNA (U 869), Institut Européen de Chimie et Biologie, 2 rue Escarpit, Pessac 33600, France [2] INSERM, ARNA (U 869), France.
authors: Cameron David
authors: 0000000207767947
authors: CD
authors: Mackereth
authors: 1] University of Bordeaux, CBMN (UMR 5248), Institut Européen de Chimie et Biologie, 2 rue Escarpit, Pessac 33600, France [2] CNRS, CBMN (UMR 5248), France.
authors: Michel
authors: M
authors: Laguerre
authors: 1] University of Nantes, CEISAM (UMR 6230), Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, Nantes Cedex 3 44322, France [2] CNRS, CEISAM (UMR 6230), France.
authors: Didier
authors: D
authors: Dubreuil
authors: 1] University of Bordeaux, CBMN (UMR 5248), Institut Européen de Chimie et Biologie, 2 rue Escarpit, Pessac 33600, France [2] CNRS, CBMN (UMR 5248), France.
authors: Ivan
authors: I
authors: Huc
mesh_terms: D000577:Amides / Q000737:chemistry*; D005632:Fructose / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D013057:Spectrum Analysis / Q000379:methods*
chemical_list: D000577:Amides; D005632:Fructose