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Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers

Two α‐aminoisobutyric acid (Aib) foldamers bearing Zn(II)‐chelating N‐termini have been synthesized and compared with a reported Aib foldamer that has a bis(quinolinyl)/mono(pyridyl) cap (BQPA group). Replacement of the quinolinyl arms of the BQPA‐capped foldamer with pyridyl gave a BPPA‐capped fold...

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Autores principales: Eccles, Natasha, della Sala, Flavio, Le Bailly, Bryden A. F., Whitehead, George F. S., Clayden, Jonathan, Webb, Simon J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7080544/
https://www.ncbi.nlm.nih.gov/pubmed/32195074
http://dx.doi.org/10.1002/open.201900362
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author Eccles, Natasha
della Sala, Flavio
Le Bailly, Bryden A. F.
Whitehead, George F. S.
Clayden, Jonathan
Webb, Simon J.
author_facet Eccles, Natasha
della Sala, Flavio
Le Bailly, Bryden A. F.
Whitehead, George F. S.
Clayden, Jonathan
Webb, Simon J.
author_sort Eccles, Natasha
collection PubMed
description Two α‐aminoisobutyric acid (Aib) foldamers bearing Zn(II)‐chelating N‐termini have been synthesized and compared with a reported Aib foldamer that has a bis(quinolinyl)/mono(pyridyl) cap (BQPA group). Replacement of the quinolinyl arms of the BQPA‐capped foldamer with pyridyl gave a BPPA‐capped foldamer, then further replacement of the linking pyridyl with a 1,2,3‐triazole gave a BPTA‐capped foldamer. Their ability to relay chiral information from carboxylate bound to Zn(II) at the N‐terminus to a glycinamide‐based NMR reporter of conformational preference at the C‐terminus was measured. The importance of the quinolinyl arms became readily apparent, as the foldamers with pyridyl arms were unable to report on the presence of chiral carboxylate in acetonitrile. Low solubility, X‐ray crystallography and (1)H NMR spectroscopy suggested that interfoldamer interactions inhibited carboxylate binding. However changing solvent to methanol revealed that the end‐to‐end relay of chiral information could be observed for the Zn(II) complex of the BPTA‐capped foldamer at low temperature.
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spelling pubmed-70805442020-03-19 Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers Eccles, Natasha della Sala, Flavio Le Bailly, Bryden A. F. Whitehead, George F. S. Clayden, Jonathan Webb, Simon J. ChemistryOpen Full Papers Two α‐aminoisobutyric acid (Aib) foldamers bearing Zn(II)‐chelating N‐termini have been synthesized and compared with a reported Aib foldamer that has a bis(quinolinyl)/mono(pyridyl) cap (BQPA group). Replacement of the quinolinyl arms of the BQPA‐capped foldamer with pyridyl gave a BPPA‐capped foldamer, then further replacement of the linking pyridyl with a 1,2,3‐triazole gave a BPTA‐capped foldamer. Their ability to relay chiral information from carboxylate bound to Zn(II) at the N‐terminus to a glycinamide‐based NMR reporter of conformational preference at the C‐terminus was measured. The importance of the quinolinyl arms became readily apparent, as the foldamers with pyridyl arms were unable to report on the presence of chiral carboxylate in acetonitrile. Low solubility, X‐ray crystallography and (1)H NMR spectroscopy suggested that interfoldamer interactions inhibited carboxylate binding. However changing solvent to methanol revealed that the end‐to‐end relay of chiral information could be observed for the Zn(II) complex of the BPTA‐capped foldamer at low temperature. John Wiley and Sons Inc. 2020-03-18 /pmc/articles/PMC7080544/ /pubmed/32195074 http://dx.doi.org/10.1002/open.201900362 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Eccles, Natasha
della Sala, Flavio
Le Bailly, Bryden A. F.
Whitehead, George F. S.
Clayden, Jonathan
Webb, Simon J.
Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers
title Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers
title_full Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers
title_fullStr Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers
title_full_unstemmed Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers
title_short Molecular Recognition by Zn(II)‐Capped Dynamic Foldamers
title_sort molecular recognition by zn(ii)‐capped dynamic foldamers
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7080544/
https://www.ncbi.nlm.nih.gov/pubmed/32195074
http://dx.doi.org/10.1002/open.201900362
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