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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SCOPUS
- 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
- Kim, YK; Lee, HN; Singh, NJ; Choi, HJ; Xue, JY; Kim, KS; Yoon, J; Hyun, MH
- Date Issued
- 2008-01-04
- Publisher
- AMER CHEMICAL SOC
- Abstract
- [GRAPHICS] 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.
- Keywords
- LIQUID-CHROMATOGRAPHIC ENANTIOSEPARATION; FLUORESCENT SENSORS; ENANTIOSELECTIVE RECOGNITION; MOLECULAR RECOGNITION; ANION RECOGNITION; MANDELIC-ACID; RECEPTORS; CHEMOSENSORS; AMPLIFICATION; CARBOXYLATES
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/23020
- DOI
- 10.1021/JO7022813
- ISSN
- 0022-3263
- Article Type
- Article
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 1, page. 301 - 304, 2008-01-04
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- There are no files associated with this item.
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