Anthracene derivatives bearing thiourea and glucopyranosyl groups for the highly selective chiral recognition of amino acids: opposite chiral selectivities from similar binding units.
Two new anthracene thiourea derivatives, 1 and 2, were investigated as fluorescent chemosensors for the chiral recognition of the two enantiomers of alpha-amino carboxylates. Especially, host 2 displayed K(L)/K(D) 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-pi 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.
Department of Chemistry, Pusan National University, Pusan 609-735, Korea.
Yun Kyoung
YK
Kim
Han Na
HN
Lee
N Jiten
NJ
Singh
Hee Jung
HJ
Choi
Jin Ying
JY
Xue
Kwang S
KS
Kim
Juyoung
J
Yoon
Myung Ho
MH
Hyun
D000596:Amino Acids / Q000737:chemistry*; D000873:Anthracenes / Q000737:chemistry*; D001665:Binding Sites; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D008968:Molecular Conformation; D012015:Reference Standards; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000596:Amino Acids; D000873:Anthracenes; C034020:anthracene; D013890:Thiourea; D005947:Glucose