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Enantioselective amino acid recognition using acyclic thiourea receptors

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
0300-922X
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
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), 1258-1263. (doi:10.1039/b102298a).

Record type: Article

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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More information

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
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 15 Feb 2006
Last modified: 10 Dec 2019 01:51

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Contributors

Author: Graham M. Kyne
Author: Mark E. Light ORCID iD
Author: Javier de Mendoza
Author: Jeremy D. Kilburn

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