Cu-Catalyzed α‑Alkylation of Glycine Derivatives for C(sp3)–H/C(sp3)–H Bond Selective Functionalization

Herein, we present the example of Cu-catalyzed oxidation coupling of amino acids/peptides for producing α-alkylated unnatural glycine derivatives by the activation of double C­(sp3)–H/C­(sp3)–H bonds. It is worth mentioning that the tractable conditions and good functional group tolerance allow the...

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Published inACS catalysis Vol. 14; no. 1; pp. 522 - 532
Main Authors Xiang, Huan, Ye, Yang
Format Journal Article
LanguageEnglish
Published American Chemical Society 05.01.2024
Subjects
C−H bond
coupling
peptide
HDACs
radical
glycine
copper
HAT
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ISSN2155-5435
2155-5435
DOI10.1021/acscatal.3c04974

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Abstract Herein, we present the example of Cu-catalyzed oxidation coupling of amino acids/peptides for producing α-alkylated unnatural glycine derivatives by the activation of double C­(sp3)–H/C­(sp3)–H bonds. It is worth mentioning that the tractable conditions and good functional group tolerance allow the specific site-modification of polypeptides utilizing this strategy. The practicality of this transformation is certified by the potent preparation of a series of HDAC inhibitors (SPACAs), which performed well in the preliminary biological evaluations. A radical–radical coupling pathway was involved in the reaction based on the preliminary mechanistic studies.
AbstractList Herein, we present the example of Cu-catalyzed oxidation coupling of amino acids/peptides for producing α-alkylated unnatural glycine derivatives by the activation of double C­(sp3)–H/C­(sp3)–H bonds. It is worth mentioning that the tractable conditions and good functional group tolerance allow the specific site-modification of polypeptides utilizing this strategy. The practicality of this transformation is certified by the potent preparation of a series of HDAC inhibitors (SPACAs), which performed well in the preliminary biological evaluations. A radical–radical coupling pathway was involved in the reaction based on the preliminary mechanistic studies.
Author Ye, Yang
Xiang, Huan
AuthorAffiliation School of Pharmacy
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Keywords C−H bond
coupling
peptide
HDACs
radical
glycine
copper
HAT
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Title Cu-Catalyzed α‑Alkylation of Glycine Derivatives for C(sp3)–H/C(sp3)–H Bond Selective Functionalization
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