title: Nucleic acid chemistry in the organic phase: from functionalized oligonucleotides to DNA side chain polymers.
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.
authors.affiliation: Zernike Institute for Advanced Materials , Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Kai
authors.initials: K
authors.lastname: Liu
authors.forename: Lifei
authors.initials: L
authors.lastname: Zheng
authors.forename: Qing
authors.initials: Q
authors.lastname: Liu
authors.forename: Jan Willem
authors.initials: JW
authors.lastname: de Vries
authors.forename: Jennifer Y
authors.initials: JY
authors.lastname: Gerasimov
authors.forename: Andreas
authors.initials: A
authors.lastname: Herrmann
mesh_terms: D001483:Base Sequence; D004247:DNA / Q000737:chemistry* / Q000235:genetics; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D058105:Polymerization; D013501:Surface-Active Agents / Q000737:chemistry
chemical_list: D009841:Oligonucleotides; D009930:Organic Chemicals; D013501:Surface-Active Agents; D004247:DNA