Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction
Functionalized oligonucleotides have recently gained increased attention for incorporation in modified nucleic acid structures both for the design of aptamers with enhanced binding properties as well as the construction of catalytic DNA and RNA. As a shortcut alternative to the incorporation of mult...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.268 |
| _version_ | 1818641973021507584 |
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| author | Vicky Gheerardijn Jos Van den Begin Annemieke Madder |
| author_facet | Vicky Gheerardijn Jos Van den Begin Annemieke Madder |
| author_sort | Vicky Gheerardijn |
| collection | DOAJ |
| description | Functionalized oligonucleotides have recently gained increased attention for incorporation in modified nucleic acid structures both for the design of aptamers with enhanced binding properties as well as the construction of catalytic DNA and RNA. As a shortcut alternative to the incorporation of multiple modified residues, each bearing one extra functional group, we present here a straightforward method for direct linking of functionalized amino acids to the nucleoside base, thus equipping the nucleoside with two extra functionalities at once. As a proof of principle, we have introduced three amino acids with functional groups frequently used as key-intermediates in DNA- and RNAzymes via an efficient and straightforward domino carboxamidation reaction. |
| first_indexed | 2024-12-16T23:35:40Z |
| format | Article |
| id | doaj.art-44284464eb524111a6823a5ece37ba8c |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T23:35:40Z |
| publishDate | 2014-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-44284464eb524111a6823a5ece37ba8c2022-12-21T22:11:45ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-11-011012566257210.3762/bjoc.10.2681860-5397-10-268Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reactionVicky Gheerardijn0Jos Van den Begin1Annemieke Madder2Department of Organic and Macromolecular Chemistry, Organic and Biomimetic Chemistry Research Group, Ghent University, Krijgslaan 281 S4, 9000 Ghent, BelgiumDepartment of Organic and Macromolecular Chemistry, Organic and Biomimetic Chemistry Research Group, Ghent University, Krijgslaan 281 S4, 9000 Ghent, BelgiumDepartment of Organic and Macromolecular Chemistry, Organic and Biomimetic Chemistry Research Group, Ghent University, Krijgslaan 281 S4, 9000 Ghent, BelgiumFunctionalized oligonucleotides have recently gained increased attention for incorporation in modified nucleic acid structures both for the design of aptamers with enhanced binding properties as well as the construction of catalytic DNA and RNA. As a shortcut alternative to the incorporation of multiple modified residues, each bearing one extra functional group, we present here a straightforward method for direct linking of functionalized amino acids to the nucleoside base, thus equipping the nucleoside with two extra functionalities at once. As a proof of principle, we have introduced three amino acids with functional groups frequently used as key-intermediates in DNA- and RNAzymes via an efficient and straightforward domino carboxamidation reaction.https://doi.org/10.3762/bjoc.10.268amino acidsbioorganic chemistrycarboxamidation reactionchemically modifiedDNA nucleosidesnucleic acids |
| spellingShingle | Vicky Gheerardijn Jos Van den Begin Annemieke Madder Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction Beilstein Journal of Organic Chemistry amino acids bioorganic chemistry carboxamidation reaction chemically modified DNA nucleosides nucleic acids |
| title | Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction |
| title_full | Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction |
| title_fullStr | Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction |
| title_full_unstemmed | Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction |
| title_short | Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction |
| title_sort | versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction |
| topic | amino acids bioorganic chemistry carboxamidation reaction chemically modified DNA nucleosides nucleic acids |
| url | https://doi.org/10.3762/bjoc.10.268 |
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