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“Chemical Ligation”: A Versatile Method for Nucleoside Modification with Boron Clusters
Author(s) -
Wojtczak Błazej A.,
Andrysiak Agnieszka,
Grüner Bohumír,
Lesnikowski Zbigniew J.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801053
Subject(s) - azide , chemistry , cycloaddition , boron , nucleobase , nucleoside , nucleophile , combinatorial chemistry , ring (chemistry) , polymer chemistry , organic chemistry , stereochemistry , dna , catalysis , biochemistry
A general approach to the synthesis of nucleoside conjugates containing carborane and metallocarborane complexes, based on Huisgen 1,3‐dipolar cycloaddition (“chemical ligation”), is described. Boron‐cluster‐donors bearing terminal azide or ethynyl groups were prepared in the ring‐opening reaction of dioxane‐boron‐cluster adducts and an azide anion or suitable alkynol‐derived alcoholate nucleophile. Analogous derivatives bearing terminal sulfhydryl groups were also prepared. Nucleosides with various spacers containing terminal azide or ethynyl groups, located within nucleobases 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.