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Enantioselective binding of dipeptides using acyclic receptors

Enantioselective binding of dipeptides using acyclic receptors
Enantioselective binding of dipeptides using acyclic receptors
Novel receptors featuring a 2,6-diamidopyridine 'head' group and bearing sulfonamidopeptide sidearms have been prepared on the solid-phase; one receptor showed high selectivity for N-Cbz-D-Ala-D-AlaOH over its enantiomer N-Cbz-L-Ala-L-AlaOH, but absolute binding constants were relatively weak, which can be understood in terms of receptors which have to unfold, breaking intramolecular hydrogen bonds, in order to accommodate the guests.
synthetic receptors, tweezers, peptides
1359-7345
1358-1359
Botana, E.
4589a0fb-75c8-418c-8d8c-03a5c0cda64d
Ongeri, S.
d7ce39ca-4281-4fa1-8cb5-c9c4436cdef9
Arienzo, R.
9defe0a3-9172-4d00-8ff5-3706558427ae
Demarcus, M.
d570073b-7184-4df9-addd-ea3106232e67
Frey, J. G.
ba60c559-c4af-44f1-87e6-ce69819bf23f
Piarulli, U.
63121750-de51-4ee9-8c8b-9a5b200be324
Potenza, D.
2788a6c1-75d2-434f-8d0c-2c8a006e3c0f
Gennari, C.
6a6f57dd-5bf5-45ad-9199-4e6e7cf31f6a
Kilburn, J. D.
c02957da-baca-4138-961a-a85170d11dd8
Botana, E.
4589a0fb-75c8-418c-8d8c-03a5c0cda64d
Ongeri, S.
d7ce39ca-4281-4fa1-8cb5-c9c4436cdef9
Arienzo, R.
9defe0a3-9172-4d00-8ff5-3706558427ae
Demarcus, M.
d570073b-7184-4df9-addd-ea3106232e67
Frey, J. G.
ba60c559-c4af-44f1-87e6-ce69819bf23f
Piarulli, U.
63121750-de51-4ee9-8c8b-9a5b200be324
Potenza, D.
2788a6c1-75d2-434f-8d0c-2c8a006e3c0f
Gennari, C.
6a6f57dd-5bf5-45ad-9199-4e6e7cf31f6a
Kilburn, J. D.
c02957da-baca-4138-961a-a85170d11dd8

Botana, E., Ongeri, S., Arienzo, R., Demarcus, M., Frey, J. G., Piarulli, U., Potenza, D., Gennari, C. and Kilburn, J. D. (2001) Enantioselective binding of dipeptides using acyclic receptors. Chemical Communications, (15), 1358-1359. (doi:10.1039/b102383g).

Record type: Article

Abstract

Novel receptors featuring a 2,6-diamidopyridine 'head' group and bearing sulfonamidopeptide sidearms have been prepared on the solid-phase; one receptor showed high selectivity for N-Cbz-D-Ala-D-AlaOH over its enantiomer N-Cbz-L-Ala-L-AlaOH, but absolute binding constants were relatively weak, which can be understood in terms of receptors which have to unfold, breaking intramolecular hydrogen bonds, in order to accommodate the guests.

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More information

Published date: 2001
Additional Information: ChemComm
Keywords: synthetic receptors, tweezers, peptides

Identifiers

Local EPrints ID: 19421
URI: http://eprints.soton.ac.uk/id/eprint/19421
ISSN: 1359-7345
PURE UUID: 5804f5fe-cd8b-4cc5-9d79-c06c72f0496b
ORCID for J. G. Frey: ORCID iD orcid.org/0000-0003-0842-4302

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 03 Dec 2019 02:07

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Contributors

Author: E. Botana
Author: S. Ongeri
Author: R. Arienzo
Author: M. Demarcus
Author: J. G. Frey ORCID iD
Author: U. Piarulli
Author: D. Potenza
Author: C. Gennari
Author: J. D. Kilburn

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