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A Pyridine‐Acetylene‐Aniline Oligomer: Saccharide Recognition and Influence of this Recognition Array on the Activity as Acylation Catalyst
Author(s) -
Ohishi Yuki,
Takata Toshikazu,
Inouye Masahiko
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000603
Subject(s) - oligomer , pyridine , chemistry , aniline , acylation , acetylene , derivatization , circular dichroism , polymer chemistry , organic chemistry , photochemistry , catalysis , stereochemistry , high performance liquid chromatography
In order to create new functions of foldamer‐type hosts, various kinds of recognition arrays are expected to be developed. Here, a pyridine‐acetylene‐aniline unit is presented as a new class of a saccharide recognition array. The conformational stabilities of this array were analyzed by DFT calculation, and suggested that a pyridine‐acetylene‐aniline oligomer tends to form a helical structure. An oligomer of this array was synthesized, and its association for octyl β ‐D‐glucopyranoside was confirmed by 1 H NMR measurements. UV/Vis, circular dichroism, and fluorescence titration experiments revealed its high affinity for octyl glycosides in apolar solvents ( K a =10 4 to 10 5 M −1 ). This oligomer was relatively stable under basic conditions, and therefore this array was expected to be applied to the derivatization of saccharides. A 4‐(dialkylamino)pyridine attached pyridine‐acetylene‐aniline oligomer proved to catalyze the acylation of the octyl glucoside.