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An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside
Designing compounds for the selective molecular recognition of carbohydrates is a challenging task for supramolecular chemists. Macrocyclic compounds that incorporate isophtalamide or bisurea spacers linking two aromatic moieties have proven effective for the selective recognition of all‐equatorial...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252426/ https://www.ncbi.nlm.nih.gov/pubmed/33878234 http://dx.doi.org/10.1002/cphc.202100229 |
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author | Schaapkens, Xander Holdener, Joël H. Tolboom, Jens Bobylev, Eduard O. Reek, Joost N. H. Mooibroek, Tiddo J. |
author_facet | Schaapkens, Xander Holdener, Joël H. Tolboom, Jens Bobylev, Eduard O. Reek, Joost N. H. Mooibroek, Tiddo J. |
author_sort | Schaapkens, Xander |
collection | PubMed |
description | Designing compounds for the selective molecular recognition of carbohydrates is a challenging task for supramolecular chemists. Macrocyclic compounds that incorporate isophtalamide or bisurea spacers linking two aromatic moieties have proven effective for the selective recognition of all‐equatorial carbohydrates. Here, we explore the molecular recognition properties of an octa‐urea [Pd(2)L(4)](4+) cage complex (4). It was found that small anions like NO(3) (−) and BF(4) (−) bind inside 4 and inhibit binding of n‐octyl glycosides. When the large non‐coordinating anion ‘BAr(F)’ was used, 4 showed excellent selectivity towards n‐octyl‐α‐D‐Mannoside with binding in the order of K (a)≈16 M(−1) versus non‐measurable affinities for other glycosides including n‐octyl‐β‐D‐Glucoside (in CH(3)CN/H(2)O 91 : 9). |
format | Online Article Text |
id | pubmed-8252426 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-82524262021-07-07 An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside Schaapkens, Xander Holdener, Joël H. Tolboom, Jens Bobylev, Eduard O. Reek, Joost N. H. Mooibroek, Tiddo J. Chemphyschem Articles Designing compounds for the selective molecular recognition of carbohydrates is a challenging task for supramolecular chemists. Macrocyclic compounds that incorporate isophtalamide or bisurea spacers linking two aromatic moieties have proven effective for the selective recognition of all‐equatorial carbohydrates. Here, we explore the molecular recognition properties of an octa‐urea [Pd(2)L(4)](4+) cage complex (4). It was found that small anions like NO(3) (−) and BF(4) (−) bind inside 4 and inhibit binding of n‐octyl glycosides. When the large non‐coordinating anion ‘BAr(F)’ was used, 4 showed excellent selectivity towards n‐octyl‐α‐D‐Mannoside with binding in the order of K (a)≈16 M(−1) versus non‐measurable affinities for other glycosides including n‐octyl‐β‐D‐Glucoside (in CH(3)CN/H(2)O 91 : 9). John Wiley and Sons Inc. 2021-05-19 2021-06-16 /pmc/articles/PMC8252426/ /pubmed/33878234 http://dx.doi.org/10.1002/cphc.202100229 Text en © 2021 The Authors. ChemPhysChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Articles Schaapkens, Xander Holdener, Joël H. Tolboom, Jens Bobylev, Eduard O. Reek, Joost N. H. Mooibroek, Tiddo J. An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside |
title | An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside |
title_full | An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside |
title_fullStr | An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside |
title_full_unstemmed | An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside |
title_short | An Octa‐Urea [Pd(2)L(4)](4+) Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside |
title_sort | octa‐urea [pd(2)l(4)](4+) cage that selectively binds to n‐octyl‐α‐d‐mannoside |
topic | Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252426/ https://www.ncbi.nlm.nih.gov/pubmed/33878234 http://dx.doi.org/10.1002/cphc.202100229 |
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