Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis

Karlijn Hollanders; Evelien Renders; Charlène Gadais; Dario Masullo; Laurent Van Raemdonck; Clarence C. D. Wybon; Charlotte Martin; Wouter A. Herrebout; Bert U. W. Maes; Steven Ballet

doi:10.1021/acscatal.9b05074

Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis

Karlijn Hollanders, Evelien Renders, Charlène Gadais, Dario Masullo, Laurent Van Raemdonck, Clarence C. D. Wybon, Charlotte Martin, Wouter A. Herrebout, Bert U. W. Maes, Steven Ballet

Chemistry

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4280-4289
Number of pages	10
Journal	ACS Catalysis
Volume	10
Issue number	7
DOIs	https://doi.org/10.1021/acscatal.9b05074
Publication status	Published - 3 Apr 2020

Bibliographical note

Funding Information:
This work was financially supported by the Research Foundation Flanders (FWO) (Research Project and Scientific Research Network (WOG)), the Hercules and the Francqui Foundation, and the University of Antwerp (BOF). Computational resources were provided by the Flemish Supercomputer Centre (VSC).

Publisher Copyright:
© 2020 American Chemical Society.

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

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title = "Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis",

abstract = "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.",

author = "Karlijn Hollanders and Evelien Renders and Charl{\`e}ne Gadais and Dario Masullo and {Van Raemdonck}, Laurent and Wybon, {Clarence C. D.} and Charlotte Martin and {A. Herrebout}, Wouter and Maes, {Bert U. W.} and Steven Ballet",

note = "Funding Information: This work was financially supported by the Research Foundation Flanders (FWO) (Research Project and Scientific Research Network (WOG)), the Hercules and the Francqui Foundation, and the University of Antwerp (BOF). Computational resources were provided by the Flemish Supercomputer Centre (VSC). Publisher Copyright: {\textcopyright} 2020 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2020",

month = apr,

day = "3",

doi = "10.1021/acscatal.9b05074",

language = "English",

volume = "10",

pages = "4280--4289",

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TY - JOUR

T1 - Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis

AU - Hollanders, Karlijn

AU - Renders, Evelien

AU - Gadais, Charlène

AU - Masullo, Dario

AU - Van Raemdonck, Laurent

AU - Wybon, Clarence C. D.

AU - Martin, Charlotte

AU - A. Herrebout, Wouter

AU - Maes, Bert U. W.

AU - Ballet, Steven

N1 - Funding Information: This work was financially supported by the Research Foundation Flanders (FWO) (Research Project and Scientific Research Network (WOG)), the Hercules and the Francqui Foundation, and the University of Antwerp (BOF). Computational resources were provided by the Flemish Supercomputer Centre (VSC). Publisher Copyright: © 2020 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2020/4/3

Y1 - 2020/4/3

N2 - 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.

AB - 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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U2 - 10.1021/acscatal.9b05074

DO - 10.1021/acscatal.9b05074

M3 - Article

SN - 2155-5435

VL - 10

SP - 4280

EP - 4289

JO - ACS Catalysis

JF - ACS Catalysis

IS - 7

ER -

Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis

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