Synthesis 2024; 56(15): 2339-2346
Photoredox-Catalyzed Oxidative C–H Alkylation of Glycine Derivatives with 4-Alkyl-1,4-dihydropyridines
Madala Hari Babu‡
a
College of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea
,
Eunbin Jang‡
b
College of Pharmacy, Chungnam National University, Daejeon 34134, Republic of Korea
,
Hyesu Jang
b
College of Pharmacy, Chungnam National University, Daejeon 34134, Republic of Korea
,
Sang Kyum Kim
b
College of Pharmacy, Chungnam National University, Daejeon 34134, Republic of Korea
,
a
College of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea
c
Department of Regulatory Science, Graduate School, Kyung Hee University, Seoul 02447, Republic of Korea
d
Institute of Regulatory Innovation through Science, Kyung Hee University, Seoul 02447, Republic of Korea
› Author Affiliations This work was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (No. 2021R1C1C1010044) and a grant from the National Institute of Food and Drug Safety Evaluation in 2023 (21153MFDS601).
Abstract
Oxidative α-C(sp3 )–H alkylation of N -arylated glycine derivatives with 4-alkyldihydropyridine derivatives (alkyl-DHPs) as versatile alkyl radical precursors has been developed. Utilizing visible-light-driven photoredox catalysis and ammonium persulfate as an oxidizing agent, this methodology facilitates the site-selective alkylation of glycine derivatives, enabling the site-selective alkylation of peptides. The reaction exhibits broad substrate scope, including various alkyl radicals and acid-labile functional groups. This approach expands the synthetic toolbox in peptide chemistry, offering a mild and efficient method for the synthesis of modified peptides.
Key words
unnatural amino acids -
photocatalysis -
4-alkyl-1,4-dihydropyridines -
persulfate -
peptides
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-2284-9845.
Supporting Information
Publication History
Received: 14 February 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
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