Exploring the Chiral Recognition of Carboxylates by C2-Symmetric Receptors Bearing Glucosamine Pendant Arms.

作者: Dawid Lichosyt , Sylwia Wasiłek , Janusz Jurczak

DOI: 10.1021/ACS.JOC.6B00763

关键词:

摘要: Two urea-based receptors containing a glucosamine derivative were synthesized and investigated in terms of their ability to recognize chiral achiral anions. Both demonstrated high affinity toward carboxylates very competitive DMSO/water mixtures. The recognition properties these compounds studied using structurally differentiated guests derived from mandelic acid α-amino acids. We found that receptor 1 exhibits significantly higher enantioselectivities than compound 2 for all anions investigated, with KS/KR ratio up 2. This low enantiodiscrimination the case is attributed lack interactions between its sugar moieties side chain anions, due inadequate spatial arrangement.

参考文章(32)
Guy A. Hembury, Victor V. Borovkov, Yoshihisa Inoue, Chirality-Sensing Supramolecular Systems Chemical Reviews. ,vol. 108, pp. 1- 73 ,(2008) , 10.1021/CR050005K
Guang-Yan Qing, Yong-Bing He, Yang Zhao, Chen-Guang Hu, Shun-Ying Liu, Xi Yang, Calix[4]arene-Based Chromogenic Chemosensor for the α-Phenylglycine Anion: Synthesis and Chiral Recognition European Journal of Organic Chemistry. ,vol. 2006, pp. 1574- 1580 ,(2006) , 10.1002/EJOC.200500704
Yasmine Willener, Kévin M. Joly, Christopher J. Moody, James H. R. Tucker, An exploration of ferrocenyl ureas as enantioselective electrochemical sensors for chiral carboxylate anions. Journal of Organic Chemistry. ,vol. 73, pp. 1225- 1233 ,(2008) , 10.1021/JO701809B
Stefan Kubik, Anion recognition in water Chemical Society Reviews. ,vol. 39, pp. 3648- 3663 ,(2010) , 10.1039/B926166B
Sandra Bartoli, Tariq Mahmood, Abdul Malik, Sally Dixon, Jeremy D. Kilburn, Selective binding of L-glutamate derivative in aqueous solvents. Organic and Biomolecular Chemistry. ,vol. 6, pp. 2340- 2345 ,(2008) , 10.1039/B803089H
Guang-Yan Qing, Tao-Lei Sun, Feng Wang, Yong-Bing He, Xi Yang, Chromogenic Chemosensors for N‐Acetylaspartate Based on Chiral Ferrocene‐Bearing Thiourea Derivatives European Journal of Organic Chemistry. ,vol. 2009, pp. 841- 849 ,(2009) , 10.1002/EJOC.200800961
T. Ito, H. Ando, T. Suzuki, T. Ogura, K. Hotta, Y. Imamura, Y. Yamaguchi, H. Handa, Identification of a Primary Target of Thalidomide Teratogenicity Science. ,vol. 327, pp. 1345- 1350 ,(2010) , 10.1126/SCIENCE.1177319
Paulina Hamankiewicz, Jarosław M. Granda, Janusz Jurczak, Influence of the size and geometry of the anion binding pocket of sugar–urea anion receptors on chiral recognition Tetrahedron Letters. ,vol. 54, pp. 5608- 5611 ,(2013) , 10.1016/J.TETLET.2013.08.019
César Raposo, Marta Almaraz, Nieves Pérez, Mercedes Martín, Volker Weinrich, Manuel Grande, MaCruz Caballero, Joaquín R. Morán, Cleft type receptors for butenolides based on chromenone derivatives Tetrahedron Letters. ,vol. 37, pp. 1485- 1488 ,(1996) , 10.1016/0040-4039(96)00045-7