Enantioselective lactate binding by chiral tripodal anion hosts derived from amino acids
- 26 February 2009
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 7 (8) , 1554-1561
- https://doi.org/10.1039/b817889e
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.Keywords
This publication has 45 references indexed in Scilit:
- Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensorsCoordination Chemistry Reviews, 2006
- PrefaceCoordination Chemistry Reviews, 2006
- What Anions Do to N−H-Containing ReceptorsAccounts of Chemical Research, 2006
- Engineering emissive europium and terbium complexes for molecular imaging and sensingDalton Transactions, 2006
- A modular approach to anion binding podands: adaptability in design and synthesis leads to adaptability in propertiesChemical Communications, 2006
- Modular assembly of a preorganised, ditopic receptor for dicarboxylatesChemical Communications, 2005
- Co-transport of H+/Cl– by a synthetic prodigiosin mimicChemical Communications, 2005
- Anion‐Induced Urea DeprotonationChemistry – A European Journal, 2005
- Dual responsive chemosensors for anions: the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single moleculeTetrahedron Letters, 2003
- Functional arginyl residues as NADH binding sites of alcohol dehydrogenasesBiochemistry, 1974