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Nucleic acid chemistry in the organic phase: from functionalized oligonucleotides to DNA side chain polymers.

Authors
  • Liu, Kai
  • Zheng, Lifei
  • Liu, Qing
  • de Vries, Jan Willem
  • Gerasimov, Jennifer Y
  • Herrmann, Andreas
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Publication Date
Oct 08, 2014
Volume
136
Issue
40
Pages
14255–14262
Identifiers
DOI: 10.1021/ja5080486
PMID: 25265497
Source
Medline
License
Unknown

Abstract

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 DNA-surfactant complex as a reactive scaffold. A remarkable range of amphiphile-DNA structures (DNA-pyrene, DNA-triphenylphosphine, DNA-hydrocarbon, 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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