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Title
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Zn-catalyzed nicotinate-directed transamidations in peptide synthesis
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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ACS catalysis. - -
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Publication
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2020
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ISSN
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2155-5435
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DOI
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10.1021/ACSCATAL.9B05074
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Volume/pages
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10
:7
(2020)
, p. 4280-4289
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ISI
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000526395000030
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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