Nucleoside bearing boron clusters and their phosphoramidites – building blocks for modified oligonucleotide synthesis

Autor:	Agnieszka Kiliszek, Zbigniew J. Lesnikowski, Michal Matuszewski, Wojciech Rypniewski, Agnieszka B. Olejniczak
Rok vydání:	2015
Předmět:	Stereochemistry Chemistry chemistry.chemical_element General Chemistry Crystal structure Oligonucleotide synthesis Electrochemistry Combinatorial chemistry Catalysis Materials Chemistry Click chemistry Carborane Boron Nucleoside Conjugate
Zdroj:	New Journal of Chemistry. 39:1202-1221
ISSN:	1369-9261 1144-0546
DOI:	10.1039/c4nj01096e
Popis:	This paper describes a general method for the synthesis of four canonical nucleosides T, dC, dA and dG and their phosphoramidites suitable for automated synthesis of DNA modified with a carborane cage. A boron cluster in the form of an electroneutral, lipophilic 1,2-dicarba-closo-dodecaborane (C2B9H11) or negatively charged, redox-active 7,8-dicarba-nido-undecaborate ion (C2B9H12(−1)) was used as a modifying unit. The method is based on the “click chemistry” type Huisgen–Sharpless–Meldal reaction. All boron cluster-nucleoside conjugates have been characterized electrochemically; they have shown different redox potentials allowing for selective electrochemical identification of individual nucleosides in the mixture. There is also the first description of the crystallographic structure of the boron cluster-nucleoside conjugate: N3-{[(o-carboran-1-yl)propyl]-1N-1,2,3-triazol-4-yl}methylenethymidine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7d36877e1c85416163484cad0bc8db88 https://doi.org/10.1039/c4nj01096e Zobrazit plný text záznamu