Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of Substitution
A great number of biologically active compounds contain at least one amine function. Appropriate selectivity can only be accomplished in a few cases upon the substitution of these groups, thus functionalization of amines generally results in a mixture of them. The separation of these derivatives wit...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/9/2838 |
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| author | Panna Vezse Bianka Benda András Fekete Ádám Golcs Tünde Tóth Péter Huszthy |
| author_facet | Panna Vezse Bianka Benda András Fekete Ádám Golcs Tünde Tóth Péter Huszthy |
| author_sort | Panna Vezse |
| collection | DOAJ |
| description | A great number of biologically active compounds contain at least one amine function. Appropriate selectivity can only be accomplished in a few cases upon the substitution of these groups, thus functionalization of amines generally results in a mixture of them. The separation of these derivatives with very similar characteristics can only be performed on a preparative scale or by applying pre-optimized HPLC methods. A tris(pyridino)-crown ether was designed and synthetized for overcoming these limitations at a molecular level. It is demonstrated, that this selector molecule is able to distinguish protonated primary, secondary and tertiary amines by the formation of reversible complexes with different stabilities. This degree of substitution-specific molecular recognition of amines opens the door to develop separation processes primarily focusing on the purification of biologically active compounds in a nanomolar scale. |
| first_indexed | 2024-03-10T03:53:51Z |
| format | Article |
| id | doaj.art-94ba36b06caf4a53bdda4fcf47704153 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:53:51Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-94ba36b06caf4a53bdda4fcf477041532023-11-23T08:50:30ZengMDPI AGMolecules1420-30492022-04-01279283810.3390/molecules27092838Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of SubstitutionPanna Vezse0Bianka Benda1András Fekete2Ádám Golcs3Tünde Tóth4Péter Huszthy5Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1111 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1111 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1111 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1111 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1111 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1111 Budapest, HungaryA great number of biologically active compounds contain at least one amine function. Appropriate selectivity can only be accomplished in a few cases upon the substitution of these groups, thus functionalization of amines generally results in a mixture of them. The separation of these derivatives with very similar characteristics can only be performed on a preparative scale or by applying pre-optimized HPLC methods. A tris(pyridino)-crown ether was designed and synthetized for overcoming these limitations at a molecular level. It is demonstrated, that this selector molecule is able to distinguish protonated primary, secondary and tertiary amines by the formation of reversible complexes with different stabilities. This degree of substitution-specific molecular recognition of amines opens the door to develop separation processes primarily focusing on the purification of biologically active compounds in a nanomolar scale.https://www.mdpi.com/1420-3049/27/9/2838molecular recognitioncrown etherbiogenic amineseparation |
| spellingShingle | Panna Vezse Bianka Benda András Fekete Ádám Golcs Tünde Tóth Péter Huszthy Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of Substitution Molecules molecular recognition crown ether biogenic amine separation |
| title | Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of Substitution |
| title_full | Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of Substitution |
| title_fullStr | Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of Substitution |
| title_full_unstemmed | Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of Substitution |
| title_short | Covalently Immobilizable Tris(Pyridino)-Crown Ether for Separation of Amines Based on Their Degree of Substitution |
| title_sort | covalently immobilizable tris pyridino crown ether for separation of amines based on their degree of substitution |
| topic | molecular recognition crown ether biogenic amine separation |
| url | https://www.mdpi.com/1420-3049/27/9/2838 |
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