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Anthracene derivatives bearing thiourea and glucopyranosyl groups for the highly selective chiral recognition of amino acids: Opposite chiral selectivities from similar binding units

Title
Anthracene derivatives bearing thiourea and glucopyranosyl groups for the highly selective chiral recognition of amino acids: Opposite chiral selectivities from similar binding units
Authors
Yun K.K.Han N.L.Singh N.J.Hee J.C.Jin Y.X.Kim K.S.Yoon J.Myung H.H.
Ewha Authors
윤주영
SCOPUS Author ID
윤주영scopus
Issue Date
2008
Journal Title
Journal of Organic Chemistry
ISSN
0022-3263JCR Link
Citation
vol. 73, no. 1, pp. 301 - 304
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
(Chemical Equation Presented) Two 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 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-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. © 2008 American Chemical Society.
DOI
10.1021/jo7022813
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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