title: A threading receptor for polysaccharides.
abstract: Cellulose, chitin and related polysaccharides are key renewable sources of organic molecules and materials. However, poor solubility tends to hamper their exploitation. Synthetic receptors could aid dissolution provided they are capable of cooperative action, for example by multiple threading on a single polysaccharide molecule. Here we report a synthetic receptor designed to form threaded complexes (polypseudorotaxanes) with these natural polymers. The receptor binds fragments of the polysaccharides in aqueous solution with high affinities (K(a) up to 19,000 M(-1)), and is shown--by nuclear Overhauser effect spectroscopy--to adopt the threading geometry. Evidence from induced circular dichroism and atomic force microscopy implies that the receptor also forms polypseudorotaxanes with cellulose and its polycationic analogue chitosan. The results hold promise for polysaccharide solubilization under mild conditions, as well as for new approaches to the design of biologically active molecules.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Tiddo J
authors.initials: TJ
authors.lastname: Mooibroek
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.|Department of Chemistry and Physics, University of Almería, Carretera de Sacramento s/n, Almería 04120, Spain.
authors.forename: Juan M
authors.initials: JM
authors.lastname: Casas-Solvas
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Robert L
authors.initials: RL
authors.lastname: Harniman
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Charles M
authors.initials: CM
authors.lastname: Renney
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Tom S
authors.identifier: http://orcid.org/0000-0001-6488-1028
authors.initials: TS
authors.lastname: Carter
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Matthew P
authors.initials: MP
authors.lastname: Crump
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Anthony P
authors.initials: AP
authors.lastname: Davis
mesh_terms: D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry*; D002482:Cellulose / Q000737:chemistry; D002686:Chitin / Q000737:chemistry; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D018625:Microscopy, Atomic Force; D008958:Models, Molecular; D015394:Molecular Structure; D011134:Polysaccharides / Q000737:chemistry*; D062165:Receptors, Artificial / Q000138:chemical synthesis / Q000737:chemistry*; D012995:Solubility; D013816:Thermodynamics
chemical_list: D001672:Biocompatible Materials; D011134:Polysaccharides; D062165:Receptors, Artificial; D002686:Chitin; D002482:Cellulose