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Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water

Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water
Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water
A library of "tweezer" receptors, incorporating a guanidinium "head group" and two peptide derived side arms has been prepared on the solid-phase using an orthogonally protected guanidinium scaffold 12. The library was screened with various tripeptide derivatives in an aqueous solvent system. A tweezer receptor 25 for the side chain protected tripeptide 19 was identified from the screening experiments. Receptor 25 was resynthesised and solution binding studies were carried out, which revealed that 25 binds to tripeptide 19 with Ka = 8.2 x 10(4) +/- 2.5 x 10(4) (15 % DMSO/H2O, pH 8.75) and with appreciable selectivity over the tripeptide enantiomer 22 and the side chain deprotected tripeptide 20.
combinatorial chemistry, guanidinium, peptides, receptors, screening, molecular tweezers, artificial receptors, binding-properties, sequence, complexation, allyl, acid, part, derivatives, recognition
0009-305X
1300-1309
Jensen, Kim B.
2e68bc78-ac0f-4961-bb2b-ca0ecb769925
Braxmeier, Tobias M.
4bd6bc4d-2159-4321-a843-f2c5045d06a3
Demarcus, Mariangela
e2840343-34b4-4446-89ef-0dac6a1cfb7d
Frey, Jeremy G.
ba60c559-c4af-44f1-87e6-ce69819bf23f
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Jensen, Kim B.
2e68bc78-ac0f-4961-bb2b-ca0ecb769925
Braxmeier, Tobias M.
4bd6bc4d-2159-4321-a843-f2c5045d06a3
Demarcus, Mariangela
e2840343-34b4-4446-89ef-0dac6a1cfb7d
Frey, Jeremy G.
ba60c559-c4af-44f1-87e6-ce69819bf23f
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a

Jensen, Kim B., Braxmeier, Tobias M., Demarcus, Mariangela, Frey, Jeremy G. and Kilburn, Jeremy D. (2002) Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water. Chemistry, 8 (6), 1300-1309. (doi:10.1002/1521-3765(20020315)8:6<1300::AID-CHEM1300>3.0.CO;2-W).

Record type: Article

Abstract

A library of "tweezer" receptors, incorporating a guanidinium "head group" and two peptide derived side arms has been prepared on the solid-phase using an orthogonally protected guanidinium scaffold 12. The library was screened with various tripeptide derivatives in an aqueous solvent system. A tweezer receptor 25 for the side chain protected tripeptide 19 was identified from the screening experiments. Receptor 25 was resynthesised and solution binding studies were carried out, which revealed that 25 binds to tripeptide 19 with Ka = 8.2 x 10(4) +/- 2.5 x 10(4) (15 % DMSO/H2O, pH 8.75) and with appreciable selectivity over the tripeptide enantiomer 22 and the side chain deprotected tripeptide 20.

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More information

Published date: 2002
Keywords: combinatorial chemistry, guanidinium, peptides, receptors, screening, molecular tweezers, artificial receptors, binding-properties, sequence, complexation, allyl, acid, part, derivatives, recognition

Identifiers

Local EPrints ID: 19783
URI: http://eprints.soton.ac.uk/id/eprint/19783
ISSN: 0009-305X
PURE UUID: f0dd8466-8427-4c36-ad26-bf8e0ca8c4fd
ORCID for Jeremy G. Frey: ORCID iD orcid.org/0000-0003-0842-4302

Catalogue record

Date deposited: 20 Feb 2006
Last modified: 09 Jan 2022 02:33

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Contributors

Author: Kim B. Jensen
Author: Tobias M. Braxmeier
Author: Mariangela Demarcus
Author: Jeremy G. Frey ORCID iD
Author: Jeremy D. Kilburn

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