'Chemical Ligation': A Versatile Method for Nucleoside Modification with Boron Clusters
| Autor: | Blazej A. Wojtczak, Agnieszka Andrysiak, Zbigniew J. Lesnikowski, Bohumír Grüner |
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| Rok vydání: | 2008 |
| Předmět: |
Boron Compounds
inorganic chemicals Azides Organic Chemistry chemistry.chemical_element Nucleosides General Chemistry Ring (chemistry) Combinatorial chemistry Catalysis Cycloaddition Adduct chemistry.chemical_compound chemistry Cyclization Alkynes Carborane Organic chemistry Azide Chemical ligation Boron Nucleoside |
| Zdroj: | Chemistry - A European Journal. 14:10675-10682 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.200801053 |
| Popis: | A general approach to the synthesis of nucleoside conjugates con- taining carborane and metallocarbor- ane complexes, based on Huisgen 1,3- dipolar cycloaddition ("chemical liga- tion"), is described. Boron-cluster- donors bearing terminal azide or eth- ynyl groups were prepared in the ring- opening reaction of dioxane-boron- cluster adducts and an azide anion or suitable alkynol-derived alcoholate nu- cleophile. Analogous derivatives bear- ing terminal sulfhydryl groups were also prepared. Nucleosides with various spacers containing terminal azide or ethynyl groups, located within nucleo- bases or sugar residues, were used as boron-cluster acceptors. The proposed methodology provides a convenient way to synthesize libraries of boron- cluster-modified nucleosides for various applications. |
| Databáze: | OpenAIRE |
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