Enantioselective lactate binding by chiral tripodal anion hosts derived from amino acids.
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.
Barnard
Anna
A
Department of Chemistry, Durham University, South Road, Durham, UK DH1 3LE.
Dickson
Sara Jane
SJ
Paterson
Martin J
MJ
Todd
Adam M
AM
Steed
Jonathan W
JW