Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)–H activation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc05530c Click here for additional data file.
نویسندگان
چکیده
Cyclic peptides have attracted increasing attention in recent years due to their ability to inhibit protein– protein interactions. Current strategies to prepare cyclic peptides often rely on functional amino acid side chains or the incorporation of unnatural amino acids, thus limiting their structural diversity. Here, we describe the development of a highly versatile peptide macrocyclization strategy through a palladiumcatalyzed C(sp)–H activation and the synthesis of cyclic peptides featuring unique hydrocarbon linkages between the b-carbon of amino acids and the aromatic side chains of Phe and Trp. We demonstrate that such peptides exhibit improved biological properties compared to their acyclic counterparts. Finally, we applied this method in the synthesis of the natural product celogentin C.
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Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)-H activation.
Cyclic peptides have attracted increasing attention in recent years due to their ability to inhibit protein-protein interactions. Current strategies to prepare cyclic peptides often rely on functional amino acid side chains or the incorporation of unnatural amino acids, thus limiting their structural diversity. Here, we describe the development of a highly versatile peptide macrocyclization str...
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Room temperature C(sp2)–H oxidative chlorination via photoredox catalysis† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc03010j Click here for additional data file.
Photoredox catalysis has been developed to achieve oxidative C-H chlorination of aromatic compounds using NaCl as the chlorine source and Na2S2O8 as the oxidant. The reactions occur at room temperature and exhibit exclusive selectivity for C(sp2)-H bonds over C(sp3)-H bonds. The method has been used for the chlorination of a diverse set of substrates, including the expedited synthesis of key in...
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عنوان ژورنال:
دوره 8 شماره
صفحات -
تاریخ انتشار 2017