title: Molecular recognition of N-acetylneuraminic acid by acyclic pyridinium- and quinolinium-based receptors in aqueous media: recognition through combination of cationic and neutral recognition sites.
abstract: Compounds 5b-8b and 10b, and 11b, containing a triethylbenzene scaffold substituted with both neutral and cationic recognition sites, were shown to be effective receptors for N-acetylneuraminic acid (NeuAc), the most common occurring sialic acid, in highly competitive solvents. These compounds were established to be more powerful receptors for NeuAc than the symmetrical pyridinium- and quinolinium-based compounds 9b and 12b in aqueous media. As in natural protein-sialic acid complexes, the combination of neutral/charge-reinforced hydrogen bonds, ion pairs, CH-π, and van der Waals interactions seems to be responsible for the effective binding of this naturally widespread anionic carbohydrate in aqueous media.
authors.affiliation: Institut für Organische Chemie der Technischen Universität Freiberg, Leipziger Strasse 29, 09596 Freiberg, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Geffert
authors.forename: Matthias
authors.initials: M
authors.lastname: Kuschel
authors.forename: Monika
authors.initials: M
authors.lastname: Mazik
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002412:Cations / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry*; D011806:Quinolinium Compounds / Q000737:chemistry*; D012794:Sialic Acids / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D002412:Cations; D011726:Pyridinium Compounds; D011806:Quinolinium Compounds; D012794:Sialic Acids; D014867:Water; D019158:N-Acetylneuraminic Acid