Chemical and Ribosomal Synthesis of Topologically Controlled Bicyclic and Tricyclic Peptide Scaffolds Primed by Selenoether Formation.

Molecular Structure Peptides / chemical synthesis Ribosomes / chemistry
cyclic peptides genetic code reprogramming peptide crosslinking peptides selenocysteine

Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
01 04 2019
Historique:
received: 04 12 2018
revised: 11 02 2019
pubmed: 15 2 2019
medline: 1 9 2020
entrez: 15 2 2019
Statut: ppublish

Résumé

Bicyclic and tricyclic peptides have emerged as promising candidates for the development of protein binders and new therapeutics. However, convenient and efficient strategies that can generate topologically controlled bicyclic and tricyclic peptide scaffolds from fully-unprotected peptides are still much in demand, particularly for those amenable to the design of biosynthetic libraries. In this work, we report a reliable chemical and ribosomal synthesis of topologically controlled bicyclic and tricyclic peptide scaffolds. Our strategy involves the combination of selenoether cyclization followed by disulfide or thioether cyclization, yielding desirable bicyclic and tricyclic peptides. This work thus lays the foundation for developing peptide libraries with controlled topology of multicyclic scaffolds for in vitro display techniques.

Identifiants

DOI: 10.1002/anie.201813827 PMID: 30762292
pubmed: 30762292
doi: 10.1002/anie.201813827
doi:

Substances chimiques

Peptides 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

4880-4885

Subventions

Organisme : Japan Agency for Medical Research and Development (AMED) the Basic Science and Platform Technology Program for Innovative Biological Medicine and Platform for Drug Discovery, Informatics, and Structural Life Science
ID : am0101090j0001
Pays : International
Organisme : Japan Society for the Promotion of Science Postdoctoral Fellowship for Foreign Researchers
ID : P16412
Pays : International
Organisme : the National Natural Science Foundation of China
ID : 91853112, 21822404, 21521004
Pays : International

Informations de copyright

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Auteurs

Yizhen Yin (Y)

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo, Tokyo, 113-0033, Japan.

Qianran Fei (Q)

Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, State Key Laboratory of Physical Chemistry of Solid Surface, Xiamen University, Xiamen, 361005, P. R. China.

Weidong Liu (W)

Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, State Key Laboratory of Physical Chemistry of Solid Surface, Xiamen University, Xiamen, 361005, P. R. China.

Zhuoru Li (Z)

Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, State Key Laboratory of Physical Chemistry of Solid Surface, Xiamen University, Xiamen, 361005, P. R. China.

Hiroaki Suga (H)

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo, Tokyo, 113-0033, Japan.
ORCID: 0000-0002-5298-9186

Chuanliu Wu (C)

Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, State Key Laboratory of Physical Chemistry of Solid Surface, Xiamen University, Xiamen, 361005, P. R. China.
ORCID: 0000-0003-2946-7299

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Classifications MeSH

questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Chemical and Ribosomal Synthesis of...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › Chemical and Ribosomal Synthesis of...
questionsmedicales.fr › Cellules › Structures cellulaires › Espace intracellulaire › Cytoplasme › Structures cytoplasmiques › Organites › Ribosomes › Chemical and Ribosomal Synthesis of...