title: Synthetic Receptors for the High-Affinity Recognition of O-GlcNAc Derivatives.
abstract: The combination of a pyrenyl tetraamine with an isophthaloyl spacer has led to two new water-soluble carbohydrate receptors ("synthetic lectins"). Both systems show outstanding affinities for derivatives of N-acetylglucosamine (GlcNAc) in aqueous solution. One receptor binds the methyl glycoside GlcNAc-β-OMe with Ka ≈20,000 m(-1), whereas the other one binds an O-GlcNAcylated peptide with Ka ≈70,000 m(-1). These values substantially exceed those usually measured for GlcNAc-binding lectins. Slow exchange on the NMR timescale enabled structural determinations for several complexes. As expected, the carbohydrate units are sandwiched between the pyrenes, with the alkoxy and NHAc groups emerging at the sides. The high affinity of the GlcNAcyl-peptide complex can be explained by extra-cavity interactions, raising the possibility of a family of complementary receptors for O-GlcNAc in different contexts.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Pablo
authors.initials: P
authors.lastname: Rios
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Tom S
authors.initials: TS
authors.lastname: Carter
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. tiddomooibroek@gmail.com.
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.
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.|Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark.
authors.forename: Micke
authors.initials: M
authors.lastname: Lisbjerg
authors.affiliation: Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark.
authors.forename: Michael
authors.initials: M
authors.lastname: Pittelkow
authors.affiliation: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, USA.
authors.forename: Nitin T
authors.initials: NT
authors.lastname: Supekar
authors.affiliation: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, USA.
authors.forename: Geert-Jan
authors.initials: GJ
authors.lastname: Boons
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. Anthony.Davis@bristol.ac.uk.
authors.forename: Anthony P
authors.identifier: http://orcid.org/0000-0001-5213-624X
authors.initials: AP
authors.lastname: Davis
mesh_terms: D000117:Acetylglucosamine / Q000378:metabolism*; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy; D062165:Receptors, Artificial / Q000737:chemistry / Q000378:metabolism*
chemical_list: D062165:Receptors, Artificial; D000117:Acetylglucosamine
keywords: biomimetic hosts; carbohydrates; molecular recognition; receptors; supramolecular chemistry
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