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Solid-phase synthesis of branched oligonucleotides containing the biologically relevant dCyd341 interstrand crosslink DNA lesion

Abstract

Branched oligonucleotides containing a biological relevant DNA lesion, dCyd341 that involves an interstrand crosslink between a cytosine base on one strand and a ribose moiety of the opposite strand, was prepared in a single automated solid-phase synthesis. For this, we first prepared the phosphoramidite analogue of dCyd341 bearing an orthogonal levulinyl protecting group. Then, following synthesis of the first DNA strand containing dCyd341, levulinic group was removed and synthesis was then continued from the free base hydroxyl group at the branching point, using traditional phosphoramidites. The synthesized oligonucleotides were fully characterized by MALDI-TOF/MS, were enzymatically digested and the presence of the lesion was confirmed by LC/MS-MS and sequence was finally controlled upon exonucleases digestion followed by MALDI-TOF/MS analysis. The developed strategy was successfully employed for the preparation of several short linear and branched oligonucleotides containing the aforementioned lesion

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Supplementary files

Article information


Submitted
03 May 2019
Accepted
08 Jan 2020
First published
08 Jan 2020

Org. Biomol. Chem., 2020, Accepted Manuscript
Article type
Paper

Solid-phase synthesis of branched oligonucleotides containing the biologically relevant dCyd341 interstrand crosslink DNA lesion

M. TAVERNA PORRO, C. Saint-Pierre, D. Gasparutto and J. Ravanat, Org. Biomol. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9OB01021A

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