Diels−Alder Bioconjugation of Diene-Modified Oligonucleotides
The Journal of Organic Chemistry2001Vol. 66(16), pp. 5352–5358
Citations Over TimeTop 10% of 2001 papers
Kenneth W. Hill, Jon Taunton-Rigby, Jeffrey D. Carter, Eric Kropp, Kurt Vagle, Wolfgang A. Pieken, D. P. C. MCGEE, Gregory M. Husar, Michael Leuck, Dominic J. Anziano, David P. Sebesta
Abstract
In an effort to offer complementary technology for covalent biomolecule modification (bioconjugation), we have developed a method that exploits the aqueous acceleration of Diels--Alder reactions for this purpose. Three different diene phosphoramidite reagents have been synthesized that enable diene modification of synthetic oligonucleotides prepared by the phosphoramidite method. Clean and efficient Diels--Alder cycloaddition of these diene oligonucleotides with maleimide dieneophiles was carried out, and the labeled oligonucleotide bioconjugates were characterized by HPLC and electrospray mass spectrometry. Dieneophile stoichiometry, temperature, and pH are all parameters that were shown to influence the efficiency of the process.
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