Enantioselective lactate binding by chiral tripodal anion hosts derived from amino acids

Anna Barnard, Sara Jane Dickson, Martin J. Paterson, Adam M. Todd, Jonathan W. Steed

Research output: Contribution to journalArticle

20 Citations (Scopus)
458 Downloads (Pure)

Abstract

Chiral, tripodal anion hosts derived from either S-phenylalanine or S-leucine bind d-lactate enantioselectively. The nature of the host-guest interaction has been probed by solution NMR methods and by DFT calculations. The calculations suggest that the d-lactate may form an additional hydrogen bond in the host-guest complex while the l-lactate complex contains an intramolecular hydrogen bond. Anion binding is in competition with host dimerisation, as demonstrated by DOSY and 1H NMR spectroscopy, and DFT calculations. © 2009 The Royal Society of Chemistry.

Original languageEnglish
Pages (from-to)1554-1561
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number8
DOIs
Publication statusPublished - 2009

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