title: Substituent effects in synthetic lectins--exploring the role of CH-π interactions in carbohydrate recognition.
abstract: Contacts between aromatic surfaces and saccharide CH groups are common motifs in natural carbohydrate recognition. These CH-π interactions are modeled in "synthetic lectins" which employ oligophenyl units as apolar surfaces. Here we report the synthesis and study of new synthetic lectins with fluoro- and hydroxy-substituted biphenyl units, designed to explore the role of π-electron density in carbohydrate CH-π interactions. We find evidence that recognition can be moderated through electronic effects but that other factors such as cavity hydration are also important and sometimes predominant in determining binding strengths.
authors: School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK BS8 1TS.
authors: Nicholas P
authors: NP
authors: Barwell
authors: Anthony P
authors: AP
authors: Davis
mesh_terms: D001665:Binding Sites; D001713:Biphenyl Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004583:Electrons; D006860:Hydrogen Bonding; D037102:Lectins / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
chemical_list: D001713:Biphenyl Compounds; D002241:Carbohydrates; D037102:Lectins