A Synthetic Receptor for Choline and Carnitine

A synthetic receptor is described with the appropriate shape and size for alkylated trimethylammonium ions such as choline and carnitine. The structure features a deep, concave binding site, lined with aromatic walls that provide cation−π interactions between host and guest. Molecular mechanic calcu...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-11, Vol.124 (47), p.14014-14016
Main Authors: Ballester, Pablo, Shivanyuk, Alexander, Far, Adel Rafai, Rebek, Julius
Format: Article
Language:English
Subjects:
Biological and medical sciences
Carbamates - chemistry
Carnitine - chemistry
Cell receptors
Cell structures and functions
Choline - chemistry
Crystallography, X-Ray
Fundamental and applied biological sciences. Psychology
Models, Molecular
Molecular and cellular biology
Molecular Structure
Monoamines receptors (catecholamine, serotonine, histamine, acetylcholine)
Nuclear Magnetic Resonance, Biomolecular
Oxazolidinones - chemistry
Receptors, Cell Surface - chemistry
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Description
Summary:A synthetic receptor is described with the appropriate shape and size for alkylated trimethylammonium ions such as choline and carnitine. The structure features a deep, concave binding site, lined with aromatic walls that provide cation−π interactions between host and guest. Molecular mechanic calculations suggest that the host's shape is maintained through intermolecular hydrogen bonding with DMSO solvent molecules. The cavity is too small to accommodate larger ions. Choline and carnitine are recognized and bound with high affinity even though no complementary charges are involved in the process.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0282689