Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry
A bromoaryltetrazole-modified uridine was synthesized as a new RNA building block for bioorthogonal, light-activated and postsynthetic modification with commercially available fluorescent dyes. It allows “photoclick”-type modifications by irradiation with light (300 nm LED) at in...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-03-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/10/3/480 |
| _version_ | 1828553599082299392 |
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| author | Katja Krell Hans-Achim Wagenknecht |
| author_facet | Katja Krell Hans-Achim Wagenknecht |
| author_sort | Katja Krell |
| collection | DOAJ |
| description | A bromoaryltetrazole-modified uridine was synthesized as a new RNA building block for bioorthogonal, light-activated and postsynthetic modification with commercially available fluorescent dyes. It allows “photoclick”-type modifications by irradiation with light (300 nm LED) at internal and terminal positions of presynthesized RNA with maleimide-conjugated fluorophores in good yields. The reaction was evidenced for three different dyes. During irradiation, the emission increases due to the formation of an intrinsically fluorescent pyrazoline moiety as photoclick product. The fluorogenecity of the photoclick reaction was significantly enhanced by energy transfer between the pyrazoline as the reaction product (poor emitter) and the photoclicked dye as the strong emitter. The RNA-dye conjugates show remarkable fluorescent properties, in particular an up to 9.4 fold increase of fluorescence, which are important for chemical biology and fluorescent imaging of RNA in cells. |
| first_indexed | 2024-12-12T05:21:24Z |
| format | Article |
| id | doaj.art-45c891b9cbf243f7b991ea3ccc6806cf |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-12-12T05:21:24Z |
| publishDate | 2020-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-45c891b9cbf243f7b991ea3ccc6806cf2022-12-22T00:36:36ZengMDPI AGBiomolecules2218-273X2020-03-0110348010.3390/biom10030480biom10030480Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick ChemistryKatja Krell0Hans-Achim Wagenknecht1Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyInstitute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyA bromoaryltetrazole-modified uridine was synthesized as a new RNA building block for bioorthogonal, light-activated and postsynthetic modification with commercially available fluorescent dyes. It allows “photoclick”-type modifications by irradiation with light (300 nm LED) at internal and terminal positions of presynthesized RNA with maleimide-conjugated fluorophores in good yields. The reaction was evidenced for three different dyes. During irradiation, the emission increases due to the formation of an intrinsically fluorescent pyrazoline moiety as photoclick product. The fluorogenecity of the photoclick reaction was significantly enhanced by energy transfer between the pyrazoline as the reaction product (poor emitter) and the photoclicked dye as the strong emitter. The RNA-dye conjugates show remarkable fluorescent properties, in particular an up to 9.4 fold increase of fluorescence, which are important for chemical biology and fluorescent imaging of RNA in cells.https://www.mdpi.com/2218-273X/10/3/480photochemistrytetrazoleoligonucleotide |
| spellingShingle | Katja Krell Hans-Achim Wagenknecht Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry Biomolecules photochemistry tetrazole oligonucleotide |
| title | Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry |
| title_full | Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry |
| title_fullStr | Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry |
| title_full_unstemmed | Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry |
| title_short | Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry |
| title_sort | fluorogenic and bioorthogonal modification of rna using photoclick chemistry |
| topic | photochemistry tetrazole oligonucleotide |
| url | https://www.mdpi.com/2218-273X/10/3/480 |
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