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Symmetry 2018, 10(2), 34; https://doi.org/10.3390/sym10020034

Chiral Heterocycle-Based Receptors for Enantioselective Recognition

1
Department of Chemistry, University of Mumbai, Vidyanagari, Mumbai 400 098, India
2
Department of Chemistryand Biochemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
*
Authors to whom correspondence should be addressed.
Received: 27 December 2017 / Revised: 12 January 2018 / Accepted: 12 January 2018 / Published: 24 January 2018
(This article belongs to the Special Issue Chiral Auxiliaries and Chirogenesis)

Abstract

The majority of biomolecules found in living beings are chiral, therefore chiral molecular recognition in living systems is crucial to life. Following Cram’s seminal work on the crown-based chiral recognition, prominent research groups have reported innumerable chiral receptors with distinctly different geometrical features and asymmetry elements. Main applications of such chiral receptors are found in chiral chromatography, as for analytical purposes and for bulk separation of racemates.Incorporation of heterocyclic rings in these recognition systems added a new dimension to the existing group of receptors. Heterocycles have additional features such as availability of unshared electron pairs, pronounced conformational features, introduction of hydrogen bonding and presence of permanent dipoles as well as specific spectral properties in certain cases. These features are found to enhance binding properties of the receptors and the selectivity factors between opposite enantiomers, allowing them to be effectively separated. The review presents the synthetic approaches towards these heterocyclic receptors and their distinctly different behavior vis-à-vis carbocyclic receptors. View Full-Text
Keywords: heterocycle; receptors; enantioselective recognition; hydrogen bonding; conformational rigidity; configuration; diastereomeric interactions; macrocycle size; pyridine; dipolar interactions heterocycle; receptors; enantioselective recognition; hydrogen bonding; conformational rigidity; configuration; diastereomeric interactions; macrocycle size; pyridine; dipolar interactions
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Khose, V.N.; John, M.E.; Pandey, A.D.; Borovkov, V.; Karnik, A.V. Chiral Heterocycle-Based Receptors for Enantioselective Recognition. Symmetry 2018, 10, 34.

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