Anthracene Derivatives Bearing Thiourea and Glucopyranosyl Groups for the Highly Selective Chiral Recognition of Amino Acids: Opposite Chiral Selectivities from Similar Binding Units

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• 作者：Yun Kyoung Kim ; Han Na Lee ; N. Jiten Singh ; Hee Jung Choi ; Jin Ying Xue ; Kwang S. Kim ; Juyoung Yoon ; Myung Ho Hyun
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 4, 2008
• 年：2008
• 卷：73
• 期：1
• 页码：301 - 304
• 全文大小：144K
• 年卷期：v.73,no.1(January 4, 2008)
• ISSN：1520-6904

文摘

jo7022813n00001>Two new anthracene thiourea derivatives, 1 and 2, wereinvestigated as fluorescent chemosensors for the chiralrecognition of the two enantiomers of -amino carboxylates.Especially, host 2 displayed K_L/K_D values as high as 10.4with t-Boc alanine. Furthermore, the D/L selectivity of hosts1 and 2 is opposite, even though both hosts bear the sameglucopyranosyl units. These intriguing opposite D/L bindingaffinities by 1 and 2 were obtained without/with H-interaction between anthrancene moiety and the methylgroups, which were explained by extensive high-leveltheoretical investigations taking into account the dispersionenergy as well as the 2D-NMR chemical shifts.