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Template-Directed Quantitative One-Pot Synthesis of Homochiral Helical Receptors Enabling Enantioselective Binding
Kyung Mog Kim1, Geunmoo Song1, Seungwon Lee1
1Department of Chemistry, Yonsei University, Seoul, 03722, Republic of Korea.
Angewandte Chemie (International Ed. in English)
|August 28, 2020
Summary
Researchers created homochiral helical cavities in foldamers using template-directed synthesis. These receptors selectively bind chiral molecules, demonstrating significant differences in binding affinity for enantiomers.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Chemical Crystallography
Background:
- Aromatic foldamers offer a versatile platform for constructing complex molecular architectures.
- Template-directed synthesis and dynamic covalent chemistry are powerful tools for controlling molecular assembly.
- Achieving enantioselective recognition within synthetic receptors remains a significant challenge.
Purpose of the Study:
- To develop a one-pot method for synthesizing homochiral helical cavities within aromatic foldamers.
- To investigate the enantioselective binding capabilities of the synthesized helical receptors.
- To characterize the structures and binding modes of the receptors and their complexes.
Main Methods:
- Template-directed synthesis utilizing chiral templates (tartaric acid and sorbitol).
- Dynamic covalent chemistry, specifically imine formation and [4+2] cycloaddition.
- One-pot sequential reactions including chain elongation, template-induced folding, and cycloaddition.
- Structural characterization using single-crystal X-ray crystallography and 1H NMR spectroscopy.
Main Results:
- Quantitative one-pot synthesis of homochiral helical receptors (P-1, M-1, P-2, M-2) was achieved.
- The receptors demonstrated enantioselective binding towards the chiral templates used in their synthesis.
- Differences in association constants between enantiomeric guests exceeded two orders of magnitude.
- Detailed structural and binding information was obtained via X-ray crystallography and NMR.
Conclusions:
- Template-directed dynamic covalent chemistry enables efficient synthesis of homochiral helical foldamer receptors.
- These receptors exhibit high enantioselectivity in binding chiral guests.
- The study provides a robust strategy for designing synthetic receptors with tailored chiral recognition properties.
Keywords:
aromatic foldamerschiral guestsenantioselective bindinghomochiral receptorsmolecular recognitionMore Related Videos
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