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Issue 25, 2018
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Synthesis of comb-shaped DNA using a non-nucleosidic branching phosphoramidite

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Branched DNAs (bDNAs) having comb-like structures have found wide utility in molecular diagnostics and DNA nanotechnology. bDNAs can be generated either by designing and assembling linear DNA molecules into rigid non-covalent structures or by using an orthogonally protected branching unit to synthesize covalently linked structures. Despite the advantages of the covalently linked structures, use of this motif has been hampered by the challenging synthesis of appropriately protected branching monomers. We report the facile synthesis of a branching monomer having orthogonal DMT and Lev protecting groups using readily available δ-velarolactone and 1,3-diaminopropan-2-ol. Using this branching monomer, a comb-shaped bDNA was synthesized having three different DNA arms. The synthesis and hybridization capability of the bDNA was assessed by fluorescence microscopy using fluorescently labeled complementary and mismatched DNA probes. Convenient access to an orthogonally protected branching monomer is anticipated to accelerate applications of bDNAs in applications including diagnostics, biosensing, gene-profiling, DNA computing, multicolor imaging, and nanotechnology.

Graphical abstract: Synthesis of comb-shaped DNA using a non-nucleosidic branching phosphoramidite

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Publication details

The article was received on 13 Mar 2018, accepted on 26 May 2018 and first published on 05 Jun 2018

Article type: Paper
DOI: 10.1039/C8OB00626A
Citation: Org. Biomol. Chem., 2018,16, 4659-4664

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    Synthesis of comb-shaped DNA using a non-nucleosidic branching phosphoramidite

    S. Ellipilli, J. D. Phillips and J. M. Heemstra, Org. Biomol. Chem., 2018, 16, 4659
    DOI: 10.1039/C8OB00626A

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