JOURNAL ARTICLE

Carbonylation as a novel method for the assembly of pyrazine based oligoamide alpha-helix mimetics

Seger Van Mileghem, Brecht Egle, Philippe Gilles, Cedrick Veryser, Luc Van Meervelt, Wim M De Borggraeve
Organic & Biomolecular Chemistry 2017 January 4, 15 (2): 373-378
27910980
The design and synthesis of oligoamide α-helix peptidomimetics is reported. The oligoamide type systems are prepared in a modular fashion by coupling the monomers using palladium-catalyzed carbonylation chemistry. This enabled us to use substrates with a low nucleophilicity, leading to previously unreported pyrazine based oligoamide α-helix mimetics. The proof of principle is given by synthesizing a small set of compounds. Various end-capping groups were introduced and also a mixed multimer was successfully prepared.

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