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Preparation of Information‐Containing Macromolecules by Ligation of Dyad‐Encoded Oligomers
Author(s) -
Trinh Thanh Tam,
Oswald Laurence,
ChanSeng Delphine,
Charles Laurence,
Lutz JeanFrançois
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502414
Subject(s) - azide , macromolecule , chemistry , amide , amine gas treating , cycloaddition , combinatorial chemistry , alkyne , sequence (biology) , click chemistry , triazole , polymer chemistry , organic chemistry , biochemistry , catalysis
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 and 110 is described.