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

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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.

Originele taal-2	English
Pagina's (van-tot)	4280-4289
Aantal pagina's	10
Tijdschrift	ACS Catalysis
Volume	10
Nummer van het tijdschrift	7
DOI's	https://doi.org/10.1021/acscatal.9b05074
Status	Published - 3 apr 2020

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10.1021/acscatal.9b05074

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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",

year = "2020",

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day = "3",

doi = "10.1021/acscatal.9b05074",

language = "English",

volume = "10",

pages = "4280--4289",

journal = "ACS Catalysis",

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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

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.

UR - http://www.scopus.com/inward/record.url?scp=85084492815&partnerID=8YFLogxK

U2 - 10.1021/acscatal.9b05074

DO - 10.1021/acscatal.9b05074

M3 - Article

VL - 10

SP - 4280

EP - 4289

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 7

ER -

Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis

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