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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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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. |
format | Online Article Text |
id | pubmed-7080544 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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