Visible-Light-Driven Synthesis of Ketonyl Cysteine Compounds by Cysteine Decysteinylation with Enol Silyl Ethers Coupling

phenylphenothiazine-photocatalyzed, radical-based desulfurative addition, using the in situ-generated tetrafluoropyridyl cysteine derivative from the thiol as a key precursor, which ensures high retention of configuration. Notably, this method features simple operation: the phenothiazine photosensitizer employed in the reaction is inexpensive and readily available in comparison with costly iridium catalysts. It also boasts the advantages of easily accessible starting materials, mild reaction conditions, excellent functional group tolerance, high stereoretention, and good yields, thus exhibiting broad applicability in the modification of complex peptide molecules.

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Publication Details

Journal
Organic Letters
Published
2026-04-14
DOI
https://doi.org/10.1021/acs.orglett.6c00656
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Visible-Light-Driven Synthesis of Ketonyl Cysteine Compounds by Cysteine Decysteinylation with Enol Silyl Ethers Coupling

Qiang Zeng, Jiuzhong Huang, Xiaoxiao Yan, Weiming Chen et al.
Organic Letters
Radical Photochemical Reactions
article

Visible-Light-Driven Synthesis of Ketonyl Cysteine Compounds by Cysteine Decysteinylation with Enol Silyl Ethers Coupling

Qiang Zeng, Jiuzhong Huang, Xiaoxiao Yan, Weiming Chen, Xiaolei Wang, Da Song, Yujian Ouyang
article en

Abstract

phenylphenothiazine-photocatalyzed, radical-based desulfurative addition, using the in situ-generated tetrafluoropyridyl cysteine derivative from the thiol as a key precursor, which ensures high retention of configuration. Notably, this method features simple operation: the phenothiazine photosensitizer employed in the reaction is inexpensive and readily available in comparison with costly iridium catalysts. It also boasts the advantages of easily accessible starting materials, mild reaction conditions, excellent functional group tolerance, high stereoretention, and good yields, thus exhibiting broad applicability in the modification of complex peptide molecules.

Organic LettersVol. 28(16)
Gannan Medical University (CN), Lanzhou University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Jiangxi Province, Key Science and Technology Research Project in Jiangxi Province Department of Education
Openalex Percentile: Top 24%
Radical Photochemical Reactions
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