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Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives
The combination of a pyrenyl tetraamine with an isophthaloyl spacer has led to two new water‐soluble carbohydrate receptors (“synthetic lectins”). Both systems show outstanding affinities for derivatives of N‐acetylglucosamine (GlcNAc) in aqueous solution. One receptor binds the methyl glycoside Glc...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5026062/ https://www.ncbi.nlm.nih.gov/pubmed/26822115 http://dx.doi.org/10.1002/anie.201510611 |
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author | Rios, Pablo Carter, Tom S. Mooibroek, Tiddo J. Crump, Matthew P. Lisbjerg, Micke Pittelkow, Michael Supekar, Nitin T. Boons, Geert‐Jan Davis, Anthony P. |
author_facet | Rios, Pablo Carter, Tom S. Mooibroek, Tiddo J. Crump, Matthew P. Lisbjerg, Micke Pittelkow, Michael Supekar, Nitin T. Boons, Geert‐Jan Davis, Anthony P. |
author_sort | Rios, Pablo |
collection | PubMed |
description | The combination of a pyrenyl tetraamine with an isophthaloyl spacer has led to two new water‐soluble carbohydrate receptors (“synthetic lectins”). Both systems show outstanding affinities for derivatives of N‐acetylglucosamine (GlcNAc) in aqueous solution. One receptor binds the methyl glycoside GlcNAc‐β‐OMe with K (a)≈20 000 m (−1), whereas the other one binds an O‐GlcNAcylated peptide with K (a)≈70 000 m (−1). These values substantially exceed those usually measured for GlcNAc‐binding lectins. Slow exchange on the NMR timescale enabled structural determinations for several complexes. As expected, the carbohydrate units are sandwiched between the pyrenes, with the alkoxy and NHAc groups emerging at the sides. The high affinity of the GlcNAcyl–peptide complex can be explained by extra‐cavity interactions, raising the possibility of a family of complementary receptors for O‐GlcNAc in different contexts. |
format | Online Article Text |
id | pubmed-5026062 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-50260622016-10-03 Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives Rios, Pablo Carter, Tom S. Mooibroek, Tiddo J. Crump, Matthew P. Lisbjerg, Micke Pittelkow, Michael Supekar, Nitin T. Boons, Geert‐Jan Davis, Anthony P. Angew Chem Int Ed Engl Communications The combination of a pyrenyl tetraamine with an isophthaloyl spacer has led to two new water‐soluble carbohydrate receptors (“synthetic lectins”). Both systems show outstanding affinities for derivatives of N‐acetylglucosamine (GlcNAc) in aqueous solution. One receptor binds the methyl glycoside GlcNAc‐β‐OMe with K (a)≈20 000 m (−1), whereas the other one binds an O‐GlcNAcylated peptide with K (a)≈70 000 m (−1). These values substantially exceed those usually measured for GlcNAc‐binding lectins. Slow exchange on the NMR timescale enabled structural determinations for several complexes. As expected, the carbohydrate units are sandwiched between the pyrenes, with the alkoxy and NHAc groups emerging at the sides. The high affinity of the GlcNAcyl–peptide complex can be explained by extra‐cavity interactions, raising the possibility of a family of complementary receptors for O‐GlcNAc in different contexts. John Wiley and Sons Inc. 2016-01-28 2016-03-01 /pmc/articles/PMC5026062/ /pubmed/26822115 http://dx.doi.org/10.1002/anie.201510611 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (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 | Communications Rios, Pablo Carter, Tom S. Mooibroek, Tiddo J. Crump, Matthew P. Lisbjerg, Micke Pittelkow, Michael Supekar, Nitin T. Boons, Geert‐Jan Davis, Anthony P. Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives |
title | Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives |
title_full | Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives |
title_fullStr | Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives |
title_full_unstemmed | Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives |
title_short | Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives |
title_sort | synthetic receptors for the high‐affinity recognition of o‐glcnac derivatives |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5026062/ https://www.ncbi.nlm.nih.gov/pubmed/26822115 http://dx.doi.org/10.1002/anie.201510611 |
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