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Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis

Tijdschriftbijdrage - Tijdschriftartikel

A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide.

Tijdschrift: ACS Catalysis
ISSN: 2155-5435
Issue: 7
Volume: 10
Pagina's: 4280-4289
Jaar van publicatie:2020
CSS-citation score:3
Toegankelijkheid:Closed