Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether
Tryptophan fulfills a plethora of important functions in nature both in its free form and as a component of peptides and proteins. Selective binding of tryptophan is therefore important for diagnostic and medicinal applications. Recently, we reported a glucose naphtho crown ether which is a chemosel...
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| Language: | English |
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Beilstein-Institut
2025-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.42 |
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| author | Gianpaolo Gallo Bartosz Lewandowski |
| author_facet | Gianpaolo Gallo Bartosz Lewandowski |
| author_sort | Gianpaolo Gallo |
| collection | DOAJ |
| description | Tryptophan fulfills a plethora of important functions in nature both in its free form and as a component of peptides and proteins. Selective binding of tryptophan is therefore important for diagnostic and medicinal applications. Recently, we reported a glucose naphtho crown ether which is a chemoselective receptor for the esters of aromatic amino acids, in particular tryptophan, in water. Herein, we demonstrate that the same compound also binds free tryptophan selectively in aqueous media. Furthermore, it is capable of binding to tryptophan within model tripeptides. The naphthalene functionality in the glucose-derived receptor enables the study of guest binding using fluorescence spectroscopy. |
| format | Article |
| id | doaj-art-abf9600dfdda49b1b6fa76bd4db4bfda |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-abf9600dfdda49b1b6fa76bd4db4bfda2025-08-20T01:54:19ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-03-0121154154610.3762/bjoc.21.421860-5397-21-42Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown etherGianpaolo Gallo0Bartosz Lewandowski1Laboratory of Organic Chemistry, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland Laboratory of Organic Chemistry, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland Tryptophan fulfills a plethora of important functions in nature both in its free form and as a component of peptides and proteins. Selective binding of tryptophan is therefore important for diagnostic and medicinal applications. Recently, we reported a glucose naphtho crown ether which is a chemoselective receptor for the esters of aromatic amino acids, in particular tryptophan, in water. Herein, we demonstrate that the same compound also binds free tryptophan selectively in aqueous media. Furthermore, it is capable of binding to tryptophan within model tripeptides. The naphthalene functionality in the glucose-derived receptor enables the study of guest binding using fluorescence spectroscopy.https://doi.org/10.3762/bjoc.21.42amino acidsmacrocyclic receptorsmolecular recognitionmonosaccharidestryptophan |
| spellingShingle | Gianpaolo Gallo Bartosz Lewandowski Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether Beilstein Journal of Organic Chemistry amino acids macrocyclic receptors molecular recognition monosaccharides tryptophan |
| title | Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether |
| title_full | Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether |
| title_fullStr | Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether |
| title_full_unstemmed | Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether |
| title_short | Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether |
| title_sort | binding of tryptophan and tryptophan containing peptides in water by a glucose naphtho crown ether |
| topic | amino acids macrocyclic receptors molecular recognition monosaccharides tryptophan |
| url | https://doi.org/10.3762/bjoc.21.42 |
| work_keys_str_mv | AT gianpaologallo bindingoftryptophanandtryptophancontainingpeptidesinwaterbyaglucosenaphthocrownether AT bartoszlewandowski bindingoftryptophanandtryptophancontainingpeptidesinwaterbyaglucosenaphthocrownether |