Academic Journal

Zn-catalyzed nicotinate-directed transamidations in peptide synthesis

التفاصيل البيبلوغرافية
العنوان: Zn-catalyzed nicotinate-directed transamidations in peptide synthesis
المؤلفون: Hollanders, Karlijn, Renders, Evelien, Gadais, Charlène, Masullo, Dario, Van Raemdonck, Laurent, Wybon, Clarence, Martin, Charlotte, Herrebout, Wouter, Maes, Bert, Ballet, Steven
المصدر: 2155-5435 ; ACS catalysis
سنة النشر: 2020
المجموعة: IRUA - Institutional Repository van de Universiteit Antwerpen
مصطلحات موضوعية: Chemistry
الوصف: 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.
نوع الوثيقة: article in journal/newspaper
اللغة: English
Relation: info:eu-repo/semantics/altIdentifier/isi/000526395000030
الاتاحة: https://hdl.handle.net/10067/1695960151162165141
Rights: info:eu-repo/semantics/closedAccess
رقم الانضمام: edsbas.5F515400
قاعدة البيانات: BASE