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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...

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Autores principales: Schaapkens, Xander, Holdener, Joël H., Tolboom, Jens, Bobylev, Eduard O., Reek, Joost N. H., Mooibroek, Tiddo J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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).
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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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