Two-Component Supramolecular Gels Derived from Amphiphilic Shape-Persistent Cyclo[6]aramides for Specific Recognition of Native Arginine

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]a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-10, Vol.53 (44), p.11834-11839
Main Authors: He, Youzhou, Xu, Min, Gao, Rongzhao, Li, Xiaowei, Li, Fengxue, Wu, Xuedan, Xu, Dingguo, Zeng, Huaqiang, Yuan, Lihua
Format: Article
Language:English
Subjects:
Amides - chemistry
Amino acids
arginine
Arginine - chemistry
Chlorides
Construction
Gelation
host-guest systems
Macrocyclic Compounds - chemistry
Models, Molecular
molecular recognition
oligoamide macrocycles
Picking
Recognition
Residues
Simulation
Strategy
supramolecular gels
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Summary: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. Picking and choosing: A supramolecular two‐component gelation system based on the amphiphilic cyclo[6]aramide macrocycle and diethylammonium chloride is reported. This system provides a modularly tunable approach for creating functional two‐component gel systems for highly specific recognition of L‐arginine (L‐Arg) from 19 other amino acids by competitive host–guest interactions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201407092