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Preparation of Information-Containing Macromolecules by Ligation of Dyad-Encoded Oligomers

Abstract : A simplified strategy for preparing non-natural information-containing polymers is reported. The concept relies on the successive ligation of oligomers that contain minimal sequence motifs. It was applied here to the synthesis of digitally-encoded poly(triazole amide)s, in which propyl and 2-methyl propyl motifs are used to code 0 and 1, respectively. A library of four oligo(triazole amide)s containing the information dyads 00, 01, 10, and 11 was prepared. These oligomers contain two reactive functions, that is, an alkyne and a carboxylic acid. Thus, they can be linked to another with the help of a reactive spacer containing azide and amine functions. Using two successive chemoselective steps, that is, azide-alkyne Huisgen cycloaddition and carboxylic acid-amine coupling, monodisperse polymers can be obtained. In particular, the library of dyads permits the implementation of any desired sequence using a small number of steps. As a proof-of-concept, the synthesis of molecular bytes 00000000 and 00000110 is described.
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Submitted on : Tuesday, February 7, 2017 - 5:36:40 PM
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Thanh Tam Trinh, Laurence Oswald, Delphine Chan-Seng, Laurence Charles, Jean-François Lutz. Preparation of Information-Containing Macromolecules by Ligation of Dyad-Encoded Oligomers. Chemistry - A European Journal, Wiley-VCH Verlag, 2015, 21 (34), pp.11961--11965. ⟨10.1002/chem.201502414⟩. ⟨hal-01460650⟩

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