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Novel enantioselective receptors for N-protected glutamate and aspartate

Novel enantioselective receptors for N-protected glutamate and aspartate
Novel enantioselective receptors for N-protected glutamate and aspartate
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.
enantioselectivity, receptors, solvent effects molecular-force field, face aromatic interactions, functional-grouparrays, van-der-waals, synthetic receptors, noncovalent interactions, conformational energies, thermodynamic analysis, chiral recognition, anion recognition
0947-6539
5674-5688
Ragusa, Andrea
40dd8ad1-0a88-4d20-aa51-6949d302d363
Rossi, Sara
92f6c933-0e33-44a4-b6f8-341aadbaf98a
Hayes, Joseph M.
5625a2a2-401e-43a2-baf7-4f3300180076
Stein, Matthias
84c0deaf-35fd-4252-afb2-bf7dec83d5d8
Kilburn, Jeremy D.
88d0d1ef-fb42-4928-b7cb-792104a7b48b
Ragusa, Andrea
40dd8ad1-0a88-4d20-aa51-6949d302d363
Rossi, Sara
92f6c933-0e33-44a4-b6f8-341aadbaf98a
Hayes, Joseph M.
5625a2a2-401e-43a2-baf7-4f3300180076
Stein, Matthias
84c0deaf-35fd-4252-afb2-bf7dec83d5d8
Kilburn, Jeremy D.
88d0d1ef-fb42-4928-b7cb-792104a7b48b

Ragusa, Andrea, Rossi, Sara, Hayes, Joseph M., Stein, Matthias and Kilburn, Jeremy D. (2005) Novel enantioselective receptors for N-protected glutamate and aspartate. Chemistry - A European Journal, 11 (19), 5674-5688. (doi:10.1002/chem.200500444).

Record type: Article

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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More information

Published date: 19 September 2005
Keywords: enantioselectivity, receptors, solvent effects molecular-force field, face aromatic interactions, functional-grouparrays, van-der-waals, synthetic receptors, noncovalent interactions, conformational energies, thermodynamic analysis, chiral recognition, anion recognition

Identifiers

Local EPrints ID: 20892
URI: http://eprints.soton.ac.uk/id/eprint/20892
ISSN: 0947-6539
PURE UUID: 772ae743-49ff-43a3-9309-f3b64879cfbf

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Date deposited: 02 Mar 2006
Last modified: 15 Jul 2019 19:25

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Contributors

Author: Andrea Ragusa
Author: Sara Rossi
Author: Joseph M. Hayes
Author: Matthias Stein
Author: Jeremy D. Kilburn

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