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Synthesis
DOI: 10.1055/a-2284-9845
paper

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
,
Jaehoon Sim  ∗
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 AffiliationsThis 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).
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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

Accepted after revision: 11 March 2024

Accepted Manuscript online:
11 March 2024

Article published online:
02 April 2024

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