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Nat Chem. 2015 Apr;7(4):334-41. doi: 10.1038/nchem.2195. Epub 2015 Mar 16.

Iterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose.

Author information

1
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.
2
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.
3
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.
4
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.

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.

PMID:
25803472
DOI:
10.1038/nchem.2195
[Indexed for MEDLINE]

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