Synthesis and Diversification of Macrocyclic Alkynediyl Sulfide Peptides

Autor:	Clémentine Minozzi, Noémie Beaucage, Mathieu Morency, Javier Guerrero‐Morales, Shawn K. Collins, Antoine Caron, Sacha Nguyen Thanh, Xavier Abel-Snape, Jeffrey Santandrea, Éric Godin, Bastien Rey
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Azides Molecular Structure Sulfide 010405 organic chemistry Organic Chemistry Halide General Chemistry Tripeptide Sulfides 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis Cycloaddition 0104 chemical sciences chemistry Coordination Complexes Alkynes Peptides S oxidation Copper
Zdroj:	Chemistry – A European Journal. 26:14575-14579
ISSN:	1521-3765 0947-6539
Popis:	The synthesis of rare macrocyclic alkynediyl sulfides by a Cu-catalyzed Csp -S cross-coupling is presented. The catalytic protocol (Cu(MeCN)4 PF6 /dtbbpy) promotes macrocyclization of peptides, dipeptides and tripeptides at ambient temperature (14 examples, 23→73 % yields) via thiols and bromoalkynes, and is chemoselective with regards to terminal alkynes. Importantly, the underexplored alkynediyl sulfide functionality incorporates a rigidifying structural element and opens new opportunities for diversification of macrocyclic frameworks through S oxidation, halide addition and azide-alkyne cycloaddition chemistries to integrate sulfones, halides or valuable fluorophores (7 examples, 37→92 % yields).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::639237e43dbc3e6e7d75cfb34af3e0e7 https://doi.org/10.1002/chem.202003655 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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