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Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates
Author(s) -
Adhikari Birendra Babu,
Fujii Ayu,
Schramm Michael P.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400025
Subject(s) - chemistry , calixarene , supramolecular chemistry , molecule , molecular recognition , membrane , ion transporter , membrane transport , combinatorial chemistry , phase (matter) , small molecule , conjugate , organic chemistry , biochemistry , mathematical analysis , mathematics
A series of supramolecular calixarenes efficiently transport distinct molecular species through a liquid membrane when attached to a receptor‐complementary choline handle. Calix[6]arene hexacarboxylic acid was highly effective at transporting different target molecules against a pH gradient. Both carboxylic‐ and phosphonic‐acid‐functionalized calix[4]arenes effect transport without requiring a pH or ion gradient. NMR binding studies, two‐phase solvent extraction, and three‐phase transport experiments reveal the necessary and subtle parameters to effect the transport of molecules attached to a choline “handle”. On the other hand, rescorin[4]arene cavitands, which have similar guest recognition profiles, did not transport guest molecules. These developments reveal new approaches towards attempting synthetic‐receptor‐mediated selective small‐molecule transport in vesicular and cellular systems.