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Synfacts 2025; 21(01): 103
DOI: 10.1055/a-2467-6260
Peptide Chemistry

Synthesis of Unnatural Amino Acids and Peptides via Desulfurative Alkylation of Cysteine Derivatives

Contributor(s):
Hisashi Yamamoto
,
Kotaro Ishihara
Xu P *, Liu Y-Q, Jiang H-X, Hao T-Z, Yan S-Y, Liu Z-T, Zhu X *. Xuzhou Medical University and Soochow University, Suzhou, P. R. China
Photoinduced Radical Approach for Desulfurative Alkylation of Cysteine Derivatives to Make Unnatural Amino Acids.

Org. Lett. 2024;
26: 8854-8859
DOI: 10.1021/acs.orglett.4c03285
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Keywords

desulfurative alkylation - cysteine derivatives - unnatural amino acids

Significance

Unnatural amino acids are important and valuable building blocks in organic synthesis and medicinal chemistry. The authors developed a photocatalytic radical approach for desulfurative alkylation of cysteine derivatives with arenethiol as the hydrogen-atom-transfer catalyst for the synthesis of unnatural amino acids and peptides.


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Comment

A variety of unnatural amino acids and peptides were synthesized from cysteine derivatives by way of this desulfurative alkylation. Products that retained the stereocenter were obtained.


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Publication History

Article published online:
20 December 2024

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