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Synthesis of Non-Natural Sequence-Encoded Polymers Using Phosphoramidite Chemistry

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† Precision Macromolecular Chemistry, Institut Charles Sadron, UPR-22 CNRS, BP 84047, 23 rue du Loess, 67034 Strasbourg Cedex 2, France
‡ Aix-Marseille Université, CNRS, Institute of Radical Chemistry, UMR 7273, 13397 Marseille Cedex 20, France
*[email protected]
Cite this: J. Am. Chem. Soc. 2015, 137, 16, 5629–5635
Publication Date (Web):April 8, 2015
https://doi.org/10.1021/jacs.5b02639
Copyright © 2015 American Chemical Society
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    Abstract

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    Sequence-defined non-natural polyphosphates were prepared using iterative phosphoramidite protocols on a polystyrene solid support. Three monomers were used in this work: 2-cyanoethyl (3-dimethoxytrityloxy-propyl) diisopropylphosphoramidite (0), 2-cyanoethyl (3-dimethoxytrityloxy-2,2-dimethyl-propyl) diisopropylphosphoramidite (1), and 2-cyanoethyl (3-dimethoxytrityloxy-2,2-dipropargyl-propyl) diisopropylphosphoramidite (1′). Phosphoramidite coupling steps allowed rapid synthesis of homopolymers and copolymers. In particular, the comonomers (0, 1), (0, 1′), and (1, 1′) were used to synthesize sequence-encoded copolymers. It was found that long encoded sequences could be easily built using phosphoramidite chemistry. ESI-HRMS, MALDI-HRMS, NMR, and size exclusion chromatography analyses indicated the formation of monodisperse polymers with controlled comonomer sequences. The polymers obtained with the comonomers (0, 1′) and (1, 1′) were also modified by copper-catalyzed azide–alkyne cycloaddition with a model azide compound, namely 11-azido-3,6,9-trioxaundecan-1-amine. 1H and 13C NMR analysis evidenced quantitative modification of the alkyne side-chains of the monodisperse copolymers. Thus, the molecular structure of the coding monomer units can be easily varied after polymerization. Altogether, the present results open up interesting avenues for the design of information-containing macromolecules.

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