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Photocontrolled Synthesis of Abiotic Sequence-Defined Oligo(Phosphodiester)s

Abstract : A photoregulated phosphoramidite iterative process is studied for the synthesis of non-natural, digitally encoded oligo(phosphodiester)s. The oligomers are prepared using two reactive phosphoramidite monomers containing a 2-(2-nitrophenyl)propoxycarbonyl (NPPOC) protected OH group. The stepwise synthesis is performed on an OH-functional soluble polystyrene support, which allows recycling by precipitation in a nonsolvent. Repeating cycles involving phosphoramidite coupling, oxidation of phosphite to phosphate, and NPPOC deprotection by light irradiation at lambda = 365 nm are performed in order to prepare oligomers with different lengths and sequences. Synthesis is conducted on a micromolar scale and good recycling yields are obtained in all cases. The use of a soluble polymer support allows an in-depth characterization of the NPPOC photo-deprotection step by H-1 NMR, UV spectroscopy, and size exclusion chromatography, and thus identification of optimal synthesis conditions. After cleavage from the support, the oligo(phosphodiester)s are characterized by tandem mass spectrometry, which confirms preparation of uniform sequence-coded oligomers.
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Submitted on : Monday, April 23, 2018 - 2:42:02 PM
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Niklas Felix Konig, Sofia Telitel, Salome Poyer, Laurence Charles, Jean-Francois Lutz. Photocontrolled Synthesis of Abiotic Sequence-Defined Oligo(Phosphodiester)s. Macromolecular Rapid Communications, Wiley-VCH Verlag, 2017, 38 (24), pp.1700651. ⟨10.1002/marc.201700651⟩. ⟨hal-01774193⟩



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