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The effect of twin‐tailed sidearms on sodium cation transport in synthetic hydraphile cation channels
Author(s) -
Shabany Hossein,
Pajewski Robert,
Abel Ernesto,
Mukhopadhyay Anindita,
Gokel George W.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380623
Subject(s) - chemistry , crystallography , stereochemistry , sodium , organic chemistry
The preparation of novel tris(macrocycle)s that transport Na + through phospholipid bilayers is reported. All of the reported structures have the following structural elements: sidechain‐macrocycle‐spacer‐macro‐cycle‐spacer‐macrocycle‐sidechain. The overall extension of the channel system is defined by the lengths of the spacer chains. The flexible sidearms are thought to be aligned with the lipid axis and opposite to the spacer chains. To the extent the spacer chains contribute to organization of the structure and isolation of the cation‐containing pore from the surrounding lipid chains, more hydrophobic chains are expected to enhance cation transport. A comparison of C 12 H 25 (CH 2 ) 12 (CH 2 ) 12 C 12 H 25 , 1, with (C 12 H 25 ) 2 N(CH 2 ) 2 (CH 2 ) 12 (CH 2 ) 12 (CH 2 )2N(C 12 H 25 ) 2 , 11, shows that the Na + transport is, indeed, enhanced.