jo7022813_si_001.pdf (1002.95 kB)
Anthracene Derivatives Bearing Thiourea and Glucopyranosyl Groups for the Highly Selective Chiral Recognition of Amino Acids: Opposite Chiral Selectivities from Similar Binding Units
journal contribution
posted on 2008-01-04, 00:00 authored by Yun Kyoung Kim, Han Na Lee, N. Jiten Singh, Hee Jung Choi, Jin Ying Xue, Kwang S. Kim, Juyoung Yoon, Myung Ho HyunTwo new anthracene thiourea derivatives, 1 and 2, were
investigated as fluorescent chemosensors for the chiral
recognition of the two enantiomers of α-amino carboxylates.
Especially, host 2 displayed Kl/Kd values as high as 10.4
with t-Boc alanine. Furthermore, the d/l selectivity of hosts
1 and 2 is opposite, even though both hosts bear the same
glucopyranosyl units. These intriguing opposite d/l binding
affinities by 1 and 2 were obtained without/with H-π
interaction between anthrancene moiety and the methyl
groups, which were explained by extensive high-level
theoretical investigations taking into account the dispersion
energy as well as the 2D-NMR chemical shifts.