1454711-19-3

Upstream product

• 1005190-89-5 5′-O-(4,4′-dimethoxytriphenylmethyl)-2′-O-azidoprop-1-yl-6-N-benzoyladenosine 

Downstream Products

• 1454711-20-6 5′-O-(4,4′-dimethoxytriphenylmethyl)-2′-O-(9H-fluoren-9-yl-methylcarbonyl)aminoprop-1-yl-6-Nbenzoyladenosine-3′-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) 

Relevant academic research and scientific papers

Oligonucleotide tagging for copper-free click conjugation

Copper-free click chemistry between cyclooctynes and azide is a mild, fast and selective technology for conjugation of oligonucleotides. However, technology for site-specific introduction of the requisite probes by automated protocols is scarce, while the reported cyclooctynes are large and hydrophobic. In this work, it is demonstrated that the introduction of bicyclo[6.1.0]nonyne (BCN) into synthetic oligonucleotides is feasible by standard solid-phase phosphoramidite chemistry. A range of phosphoramidite building blocks is presented for incoporation of BCN or azide, either on-support or in solution. The usefulness of the approach is demonstrated by the straightforward and high-yielding conjugation of the resulting oligonucleotides, including biotinylation, fluorescent labeling, dimerization and attachment to polymer.