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Combinatorial libraries of diamidopyridine-derived 'tweezer' receptors and sequence selective binding of peptides

Combinatorial libraries of diamidopyridine-derived 'tweezer' receptors and sequence selective binding of peptides
Combinatorial libraries of diamidopyridine-derived 'tweezer' receptors and sequence selective binding of peptides
A library of diamidopyridine derived tweezer receptors with peptidic side-arms has been prepared. Screening experiments with the library and a dye-labelled tripeptide L-Glu-L-Ser-L-Val-OH showed excellent selectivity (strong binding of the dye-labelled guest to similar to ~0.2% of resin-bound library members was observed) and led to the identification of a tweezer receptor structure, which was shown to bind the tripeptide with good selectivity over related tripeptide sequences. Analogous screening experiments with the side-chain protected tripeptide L-Glu((OBu)-Bu-t)-L-Ser(Bu-t)-L-Val-OH, showed little selectivity for any particular library member. The results are discussed in relation to previous screening experiments, using the same tripeptide guests, with related tweezer receptor libraries, which differ by one methylene in the separation of the diamidopyridine unit from the peptidic side-arms of the tweezer receptors.
tweezer, receptor, peptide, combinatorial, library, carboxylic-acid terminus, solid-phase synthesis, molecular tweezers, recognition, identification, chemistry, water
0040-4020
711-719
Arienzo, R.
9defe0a3-9172-4d00-8ff5-3706558427ae
Kilburn, J.D.
266a563a-6076-4109-9436-1c66d0b02383
Arienzo, R.
9defe0a3-9172-4d00-8ff5-3706558427ae
Kilburn, J.D.
266a563a-6076-4109-9436-1c66d0b02383

Arienzo, R. and Kilburn, J.D. (2002) Combinatorial libraries of diamidopyridine-derived 'tweezer' receptors and sequence selective binding of peptides. Tetrahedron, 58 (4), 711-719. (doi:10.1016/S0040-4020(01)01111-5).

Record type: Article

Abstract

A library of diamidopyridine derived tweezer receptors with peptidic side-arms has been prepared. Screening experiments with the library and a dye-labelled tripeptide L-Glu-L-Ser-L-Val-OH showed excellent selectivity (strong binding of the dye-labelled guest to similar to ~0.2% of resin-bound library members was observed) and led to the identification of a tweezer receptor structure, which was shown to bind the tripeptide with good selectivity over related tripeptide sequences. Analogous screening experiments with the side-chain protected tripeptide L-Glu((OBu)-Bu-t)-L-Ser(Bu-t)-L-Val-OH, showed little selectivity for any particular library member. The results are discussed in relation to previous screening experiments, using the same tripeptide guests, with related tweezer receptor libraries, which differ by one methylene in the separation of the diamidopyridine unit from the peptidic side-arms of the tweezer receptors.

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More information

Published date: 21 January 2002
Keywords: tweezer, receptor, peptide, combinatorial, library, carboxylic-acid terminus, solid-phase synthesis, molecular tweezers, recognition, identification, chemistry, water

Identifiers

Local EPrints ID: 19659
URI: http://eprints.soton.ac.uk/id/eprint/19659
ISSN: 0040-4020
PURE UUID: 4a464629-5879-4f22-ab8d-9cb72608d999

Catalogue record

Date deposited: 15 Feb 2006
Last modified: 15 Jul 2019 19:26

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