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Trimodal Control of Ion‐Transport Activity on Cyclo‐oligo‐(1→6)‐β‐ D ‐glucosamine‐Based Artificial Ion‐Transport Systems
Author(s) -
Roy Arundhati,
Saha Tanmoy,
Gening Marina L.,
Titov Denis V.,
Gerbst Alexey G.,
Tsvetkov Yury E.,
Nifantiev Nikolay E.,
Talukdar Pinaki
Publication year - 2015
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.201502656
Subject(s) - glycoconjugate , chemistry , supramolecular chemistry , hydrogen bond , ion transporter , membrane , ion , glucosamine , hydrophobic effect , molecule , amide , crystallography , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry
Cyclo‐oligo‐(1→6)‐β‐ D ‐glucosamines functionalized with hydrophobic tails are reported as a new class of transmembrane ion‐transport system. These macrocycles with hydrophilic cavities were introduced as an alternative to cyclodextrins, which are supramolecular systems with hydrophobic cavities. The transport activities of these glycoconjugates were manipulated by altering the oligomericity of the macrocycles, as well as the length and number of attached tails. Hydrophobic tails of 3 different sizes were synthesized and coupled with each glucosamine scaffold through the amide linkage to obtain 18 derivatives. The ion‐transport activity increased from di‐ to tetrameric glucosamine macrocycles, but decreased further when flexible pentameric glucosamine was introduced. The ion‐transport activity also increased with increasing length of attached linkers. For a fixed length of linkers, the transport activity decreased when the number of such tails was reduced. All glycoconjugates displayed a uniform anion‐selectivity sequence: Cl − >Br − >I − . From theoretical studies, hydrogen bonding between the macrocycle backbone and the anion bridged through water molecules was observed.