Journal
NEW JOURNAL OF CHEMISTRY
Volume 39, Issue 2, Pages 1202-1221Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4nj01096e
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Funding
- National Science Centre [N N204 531739]
- European Regional Development Found under the Operational Programme Innovative Economy [POIG.01.01.02-10-107/09]
- Institute of Medical Biology PAS
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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: N-3-{[(o-carboran-1-yl)propyl]-1N-1,2,3-triazol-4-yl}methylenethymidine.
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