Nucleic
Acid Chemistry in the Organic Phase: From
Functionalized Oligonucleotides to DNA Side Chain Polymers
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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