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-pi 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.
Ballester
Pablo
P
The Skaggs Institute for Chemical Biology, The Scripps Research Institute, MB-26, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Shivanyuk
Alexander
A
Far
Adel Rafai
AR
Rebek
Julius
J
D002219:Carbamates / Q000737:chemistry*; D002331:Carnitine / Q000737:chemistry*; D002794:Choline / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D023303:Oxazolidinones / Q000737:chemistry*; D011956:Receptors, Cell Surface / Q000737:chemistry*
D002219:Carbamates; D023303:Oxazolidinones; D011956:Receptors, Cell Surface; D002794:Choline; D002331:Carnitine