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 (1)H NMR spectroscopy, and DFT calculations.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anions / metabolism
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Binding Sites
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Dimerization
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Hydrogen Bonding
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Lactic Acid / analogs & derivatives
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Lactic Acid / chemistry
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Lactic Acid / metabolism*
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Leucine / chemical synthesis*
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Leucine / chemistry
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Leucine / metabolism*
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Magnetic Resonance Spectroscopy
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Models, Molecular
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Phenylalanine / chemical synthesis*
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Phenylalanine / chemistry
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Phenylalanine / metabolism*
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Pyridines / chemical synthesis
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Pyridinium Compounds / chemical synthesis
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Pyridinium Compounds / chemistry
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Stereoisomerism
Substances
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Anions
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Pyridines
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Pyridinium Compounds
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Lactic Acid
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Phenylalanine
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Leucine