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Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C 3 ‐Symmetric Peptide Receptors
Author(s) -
Schnopp Markus,
Haberhauer Gebhard
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900510
Subject(s) - chemistry , enantiomer , chirality (physics) , selectivity , receptor , peptide , stereochemistry , imidazole , titration , combinatorial chemistry , molecular recognition , molecule , organic chemistry , biochemistry , catalysis , physics , quantum mechanics , nambu–jona lasinio model , quark , chiral symmetry breaking
A straightforward synthesis of C 3 ‐symmetric, imidazole‐containing, macrocyclic peptides with different binding arms is presented. The chirality of the backbone and the selection of adequate receptor arms make these systems highly selective receptors for α‐chiral primary organoammonium ions. Furthermore, the receptors have the ability to discriminate between enantiomeric guests with selectivity ratios of up to 87:13. The binding constants and the selectivity ratios were estimated by standard 1 H NMR titration techniques in CDCl 3 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)