Novel enantioselective receptors for N-protected glutamate and aspartate

Ragusa, A., Rossi, S., Hayes, Joseph orcid iconORCID: 0000-0002-7745-9616, Stein, M. and Kilburn, J.D. (2005) Novel enantioselective receptors for N-protected glutamate and aspartate. Chemistry - A European Journal, 11 (19). pp. 5674-5688. ISSN 09476539

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Official URL: http://dx.doi.org/10.1002/chem.200500444

Abstract

A series of chiral bisthiourea macrocycles 1-4 have been prepared and their binding properties with various dicarboxylate salts have been examined by using NMR titration and isothermal calorimetry experiments. Macrocycle 1, in particular, favours the 1:1 binding of N-protected L-glutamate and aspartate, but favours 1:2 binding of the corresponding D-amino acids in polar solvents (dimethyl sulfoxide and acetonitrile). The macrocycles, however, do not bind carboxylates at all in the less competitive solvent chloroform. The binding properties of these macrocyles are sensitive to small structural changes as demonstrated by the altered binding properties of macrocycles 2-4 compared with 1.


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