Chiral molecular recognition in a tripeptide benzylviologen cyclophane host

Julia A. Gavin, Maurie E. Garcia, Alan J. Benesi, Thomas E. Mallouk

Research output: Contribution to journalArticle

48 Scopus citations

Abstract

A cationic chiral cyclophane was synthesized and studied as a host for chiral and racemic π-donor molecules. The cyclophane host has a rigid binding cavity flanked by (S)-(valine-leucine-alanine) and N,N'-dibenzyl- 4,4'-bipyridinium subunits, which allow for hydrogen-bonding and π-stacking interactions with included aromatic guest molecules. 1H NMR binding titrations were performed with several different pharmaceutically interesting guest molecules including β-blockers, NSAIDs, and amino acids and amino acid derivatives. The host-guest complexation constants were generally small for neutral and cationic guests (0-39 M-1 at 20 °C in water/acetone mixtures. However, a (R)/(S) enantioselectivity ratio of 13 ± 5 was found for DOPA, a strongly π-donating cationic guest. Two-dimensional NOESY 1H NMR spectra confirm that (R)-DOPA binds inside the cavity of the host and that there is no measurable interaction of the cavity with (S)-DOPA under the same conditions.

Original languageEnglish (US)
Pages (from-to)7663-7669
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number22
DOIs
StatePublished - Oct 30 1998

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Gavin, J. A., Garcia, M. E., Benesi, A. J., & Mallouk, T. E. (1998). Chiral molecular recognition in a tripeptide benzylviologen cyclophane host. Journal of Organic Chemistry, 63(22), 7663-7669. https://doi.org/10.1021/jo980352c