Enantioselective amino acid recognition using acyclic thiourea receptors
Enantioselective amino acid recognition using acyclic thiourea receptors
A series of acyclic thiourea derivatives, designed to create a cleft with four hydrogen bond donors suitable for carboxylate recognition, have been prepared, and their ability to bind to N-protected amino acid carboxylate salts has been investigated. The crystal structure of one of the thioureas has been determined showing that it forms a hydrogen bonded centrosymmetric dimer in the solid-state, in a conformation appropriate for the desired binding of carboxylates. The thioureas show good discrimination between different amino acids and those thioureas incorporating chiral moieties show moderate enantioselectivity for a range of amino acid derivatives.
membrane technology, anion recognition, carboxylates, separation, solvents, mixtures, urea
1258-1263
Kyne, Graham M.
90ae2040-d2ee-4262-99b5-0b295fe63a9b
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Mike B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
de Mendoza, Javier
e82cdadc-87d7-43a1-aaba-d85adf15551b
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
2001
Kyne, Graham M.
90ae2040-d2ee-4262-99b5-0b295fe63a9b
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Mike B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
de Mendoza, Javier
e82cdadc-87d7-43a1-aaba-d85adf15551b
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Kyne, Graham M., Light, Mark E., Hursthouse, Mike B., de Mendoza, Javier and Kilburn, Jeremy D.
(2001)
Enantioselective amino acid recognition using acyclic thiourea receptors.
Journal of the Chemical Society, Perkin Transactions 1, (11), .
(doi:10.1039/b102298a).
Abstract
A series of acyclic thiourea derivatives, designed to create a cleft with four hydrogen bond donors suitable for carboxylate recognition, have been prepared, and their ability to bind to N-protected amino acid carboxylate salts has been investigated. The crystal structure of one of the thioureas has been determined showing that it forms a hydrogen bonded centrosymmetric dimer in the solid-state, in a conformation appropriate for the desired binding of carboxylates. The thioureas show good discrimination between different amino acids and those thioureas incorporating chiral moieties show moderate enantioselectivity for a range of amino acid derivatives.
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Published date: 2001
Keywords:
membrane technology, anion recognition, carboxylates, separation, solvents, mixtures, urea
Identifiers
Local EPrints ID: 19535
URI: http://eprints.soton.ac.uk/id/eprint/19535
ISSN: 0300-922X
PURE UUID: 03dd1f8d-7bbb-4127-bb73-1165f3c4ee7e
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Date deposited: 15 Feb 2006
Last modified: 16 Mar 2024 03:04
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Contributors
Author:
Graham M. Kyne
Author:
Javier de Mendoza
Author:
Jeremy D. Kilburn
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