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• W2938204401 startingPage "5073" @default.
• W2938204401 abstract "Ni/photoredox (4DPAIPN) dual catalysis enabled challenging peptide C(sp2)-O coupling reactions. Successful cross-coupling reactions were demonstrated with highly functionalized alcohols including side chains of amino acids (i.e., serine, threonine, tyrosine), trans-4-hydroxy-l-proline, alkyl alcohols, alkynylated alcohols, and carbohydrates. Coupling reactions between bromobenzoyl-capped peptides containing various side chains and either a protected serine building block or a serine-containing dipeptide also proceeded efficiently. Chemoselective C-O coupling (over C-N) was achieved in intermolecular reactions in the presence of a C-terminal primary amide. Furthermore, by judicious structural design in combination with computational modeling, we demonstrated side chain-to-tail macrocyclization of peptides containing a β-turn motif via C-O coupling. The methodology developed in this work brings new opportunities for late-stage diversification of complex linear and macrocyclic peptides." @default.
• W2938204401 created "2019-04-25" @default.
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• W2938204401 date "2019-01-01" @default.
• W2938204401 modified "2023-10-12" @default.
• W2938204401 title "Photoredox Ni-catalyzed peptide C(sp²)–O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization" @default.
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• W2938204401 doi "https://doi.org/10.1039/c9sc00694j" @default.
• W2938204401 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6524625" @default.
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