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Two‐Component Supramolecular Gels Derived from Amphiphilic Shape‐Persistent Cyclo[6]aramides for Specific Recognition of Native Arginine
Author(s) -
He Youzhou,
Xu Min,
Gao Rongzhao,
Li Xiaowei,
Li Fengxue,
Wu Xuedan,
Xu Dingguo,
Zeng Huaqiang,
Yuan Lihua
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407092
Subject(s) - amphiphile , supramolecular chemistry , chemistry , molecular recognition , arginine , guanidinium chloride , component (thermodynamics) , residue (chemistry) , amino acid , chloride , peptide , combinatorial chemistry , stereochemistry , organic chemistry , molecule , biochemistry , physics , copolymer , thermodynamics , enzyme , polymer
Abstract A unique supramolecular two‐component gelation system was constructed from amphiphilic shape‐persistent cyclo[6]aramides and diethylammonium chloride (or triethylammonium chloride). This system has the ability to discriminate native arginine from 19 other amino acids in a specific fashion. Cyclo[6]aramides show preferential binding for the guanidinium residue over ammonium groups. This specificity was confirmed by both experimental results and theoretical simulations. These results demonstrated a new modular displacement strategy, exploring the use of species‐binding hydrogen‐bonded macrocyclic foldamers for the construction of two‐component gelation systems for selective recognition of native amino acids by competitive host–guest interactions. This strategy may be amenable to developing a variety of functional two‐component gelators for specific recognition of various targeted organic molecular species.