Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 40, Pages 14255-14262Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5080486
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Funding
- European Union (European Research Council Starting Grant)
- European Union (STREP project MICREAGENTS)
- Netherlands Organization for Scientific Research (NWO-Vici Grant)
- Zernike Institute for Advanced Materials
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DNA-incorporating hydrophobic moieties can be synthesized by either solid-phase or solution-phase coupling. On a solid support the DNA is protected, and hydrophobic units are usually attached employing phosphoramidite chemistry involving a DNA synthesizer. On the other hand, solution coupling in aqueous medium results in low yields due to the solvent incompatibility of DNA and hydrophobic compounds. Hence, the development of a general coupling method for producing amphiphilic DNA conjugates with high yield in solution remains a major challenge. Here, we report an organic-phase coupling strategy for nucleic acid modification and polymerization by introducing a hydrophobic DNAsurfactant complex as a reactive scaffold. A remarkable range of amphiphileDNA structures (DNApyrene, DNAtriphenylphosphine, DNAhydrocarbon, and DNA block copolymers) and a series of new brush-type DNA side-chain homopolymers with high DNA grafting density are produced efficiently. We believe that this method is an important breakthrough in developing a generalized approach to synthesizing functional DNA molecules for self-assembly and related technological applications.
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