Constitutionally selective amplification of multicomponent 84-membered macrocyclic hosts for (−)-cytidine•H+

Mee-Kyung Chung; Kay Severin; Stephen J. Lee; Marcey L. Waters; Michel R. Gagné

doi:10.1039/C0SC00548G

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Constitutionally selective amplification of multicomponent 84-membered macrocyclic hosts for (−)-cytidine•H⁺†

Mee-Kyung Chung,^a Kay Severin,^b Stephen J. Lee,^c Marcey L. Waters^a and Michel R. Gagné*^a

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* Corresponding authors

^a Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, USA
E-mail: mgagne@unc.edu
Tel: (+1)919 962 6341

^b Institut des Sciences et Ingénieries Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland

^c US Army Research Office, P.O. Box 12211, Research Triangle Park, NC, USA

Abstract

Mixtures of dipeptide monomers create stereochemically and constitutionally complex dynamic libraries of potential receptors. When (−)-cytidine was utilized as guest an 84-membered cyclic host was amplified (70–175 fold) from a nearly undetectable initial concentration. Only the specified diastereomeric combination of the two chiral building blocks yielded a dynamic library from which the macrocyclic receptor could be amplified.

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Article information

DOI: https://doi.org/10.1039/C0SC00548G
Article type: Edge Article
Submitted: 01 Nov 2010
Accepted: 09 Jan 2011
First published: 24 Jan 2011

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Chem. Sci., 2011,2, 744-747

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Constitutionally selective amplification of multicomponent 84-membered macrocyclic hosts for (−)-cytidine•H⁺

M. Chung, K. Severin, S. J. Lee, M. L. Waters and M. R. Gagné, Chem. Sci., 2011, 2, 744 DOI: 10.1039/C0SC00548G

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