title: D3h-Symmetrical Shape-Persistent Macrocycles Consisting of Pyridine-Acetylene-Phenol Conjugates as an Efficient Host Architecture for Saccharide Recognition.
abstract: Hexagonal shape-persistent macrocycles (SPMs) consisting of three pyridine and three phenol rings linked with acetylene bonds were developed as a preorganized host for saccharide recognition by push-pull-type hydrogen bonding. Three tert-butyl or 2,4,6-triisopropylphenyl substituents were introduced on the host to suppress self-aggregation by steric hindrance. In spite of the simple architecture, association constants Kaof the host with alkyl glycoside guests reached the order of 106m-1on the basis of UV/Vis titration experiments. This glycoside recognition was much stronger than that in the cases of acyclic equivalent hosts because of the entropic advantage brought by preorganization of the hydrogen-bonding sites. Solid-liquid extraction and liquid-liquid transport through a liquid membrane were demonstrated by using native saccharides, and much preference to mannose was observed.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan.
authors.forename: Hajime
authors.identifier: http://orcid.org/0000-0002-8433-1530
authors.initials: H
authors.lastname: Abe
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan.
authors.forename: Tetsuhiro
authors.initials: T
authors.lastname: Yoneda
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Ohishi
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan.
authors.forename: Masahiko
authors.initials: M
authors.lastname: Inouye
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D006860:Hydrogen Bonding; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D019800:Phenol / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012439:Saccharin / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D047028:Macrocyclic Compounds; D011725:Pyridines; D019800:Phenol; D012439:Saccharin; D000114:Acetylene; D008358:Mannose
keywords: glycosides; host-guest systems; hydrogen bonds; macrocycles; shape-persistent macrocycles