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D 3 h ‐Symmetrical Shape‐Persistent Macrocycles Consisting of Pyridine–Acetylene–Phenol Conjugates as an Efficient Host Architecture for Saccharide Recognition
Author(s) -
Abe Hajime,
Yoneda Tetsuhiro,
Ohishi Yuki,
Inouye Masahiko
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603987
Subject(s) - pyridine , acetylene , phenol , conjugate , host (biology) , chemistry , stereochemistry , organic chemistry , biology , mathematics , ecology , mathematical analysis
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 K a of the host with alkyl glycoside guests reached the order of 10 6 m −1 on 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.