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Antiparallel Dynamic Covalent Chemistries

Matysiak, B. M., Nowak, P., Cvrtila, I., Pappas, C. G., Liu, B., Komaromy, D. & Otto, S., 17-May-2017, In : Journal of the American Chemical Society. 139, 19, p. 6744-6751 8 p.

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DOI

The ability to design reaction networks with high, but addressable complexity is a necessary prerequisite to make advanced functional chemical systems. Dynamic combinatorial chemistry has, proven to be a useful tool in achieving complexity, however with some limitations in controlling it. Herein we introduce the concept of antiparallel: chemistries, in which the same functional group can be channeled into one of two reversible chemistries depending on a controllable parameter. Such systems allow both for achieving complexity, by combinatorial chemistry,, and addressing it, by switching from one chemistry to another by controlling an external parameter. In our design the two antiparallel chemistries are thiol disulfide exchange and thio-Michael addition, sharing the thiol as the common building block. By means of oxidation and reduction the system can be reversibly switched from predominantly thio-Michael chemistry to predominantly disulfide chemistry, as well as to any intermediate state. Both chemistries operate in water, at room temperature, and at mildly basic pH, which makes them' a suitable platform for further development of systems chemistry.

Original languageEnglish
Pages (from-to)6744-6751
Number of pages8
JournalJournal of the American Chemical Society
Volume139
Issue number19
Publication statusPublished - 17-May-2017

    Keywords

  • COMBINATORIAL CHEMISTRY, SYSTEMS CHEMISTRY, SMALL-MOLECULE, SUPRAMOLECULAR CHEMISTRY, ADAPTIVE CHEMISTRY, MYOTONIC-DYSTROPHY, EXCHANGE PROCESSES, AQUEOUS-SOLUTION, IN-VITRO, LIBRARIES

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