A Highly Enantioselective Receptor for N-Protected Glutamate and Anomalous Solvent-Dependent Binding Properties

Solvation of the macrocycle by polar solvents leads to strong binding of an N‐protected excitatory amino acid neurotransmitter. A 1:1 complex forms highly enantioselectively between the macrocycle and N‐Boc‐L‐glutamate (as the dicarboxylate anion, see picture) in CH3CN and DMSO (with a larger entrop...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2002-11, Vol.41 (22), p.4233-4236
Main Authors: Rossi, Sara, Kyne, Graham M., Turner, David L., Wells, Neil J., Kilburn, Jeremy D.
Format: Article
Language:English
Subjects:
amino acids
Calorimetry
enantioselectivity
glutamate
Glutamates - chemistry
Glutamates - metabolism
Heterocyclic Compounds - chemistry
Kinetics
Models, Molecular
Molecular Conformation
Nuclear Magnetic Resonance, Biomolecular
Protein Binding
receptors
Receptors, Glutamate - chemistry
Receptors, Glutamate - metabolism
solvent effects
Solvents - chemistry
Stereoisomerism
Thiourea - analogs & derivatives
Thiourea - metabolism
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Description
Summary:Solvation of the macrocycle by polar solvents leads to strong binding of an N‐protected excitatory amino acid neurotransmitter. A 1:1 complex forms highly enantioselectively between the macrocycle and N‐Boc‐L‐glutamate (as the dicarboxylate anion, see picture) in CH3CN and DMSO (with a larger entropic driving force for binding), but no binding occurs in the less competitive solvent CDCl3.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20021115)41:22<4233::AID-ANIE4233>3.0.CO;2-D