NDLI: Photoredox Ni-catalyzed peptide C(sp2)–O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc00694j

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Photoredox Ni-catalyzed peptide C(sp2)–O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc00694j

Content Provider	Semantic Scholar
Author	Lee, Hyelee Boyer, Nicolas C. Deng, Qiaolin Kim, Hai-Young Sawyer, Tomi K. Sciammetta, Nunzio
Copyright Year	2019
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.
Starting Page	5073
Ending Page	5078
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/c9sc00694j
PubMed reference number	31183058
Journal	Medline
Volume Number	10
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc00694j
Alternate Webpage(s)	https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/04/91/SC-010-C9SC00694J.PMC6524625.pdf
Alternate Webpage(s)	http://www.rsc.org/suppdata/c9/sc/c9sc00694j/c9sc00694j1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c9sc00694j
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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