Copper-Mediated Deprotection of Thiazolidine and Selenazolidine Derivatives Applied to Native Chemical Ligation

Copper-Mediated Deprotection of Thiazolidine and Selenazolidine Derivatives Applied to Native Chemical Ligation

Cupric sulfate efficiently opens thiazolidine and selenazolidine rings, producing a protected N-terminal cysteine or selenocysteine derivative without the use of inert gas or solvent. This is a clear advantage over methods that use water-soluble palladium salts, which fail to react with the selenazo...

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Veröffentlicht in:Journal of organic chemistry 2020-02, Vol.85 (3), p.1425-1433
Hauptverfasser: Naruse, Naoto, Kobayashi, Daishiro, Ohkawachi, Kento, Shigenaga, Akira, Otaka, Akira
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container_end_page 1433
container_issue 3
container_start_page 1425
container_title Journal of organic chemistry
container_volume 85
creator Naruse, Naoto
Kobayashi, Daishiro
Ohkawachi, Kento
Shigenaga, Akira
Otaka, Akira
description Cupric sulfate efficiently opens thiazolidine and selenazolidine rings, producing a protected N-terminal cysteine or selenocysteine derivative without the use of inert gas or solvent. This is a clear advantage over methods that use water-soluble palladium salts, which fail to react with the selenazolidine ring. This copper-mediated reaction proceeds with monovalent or divalent copper ions, and disulfide bond formation followed by ring-opening promotes the process. This copper-mediated reaction, which is compatible with the standard native chemical ligation conditions, was applied to the synthesis of the 77-mer CXCL14 protein.
doi_str_mv 10.1021/acs.joc.9b02388
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title Copper-Mediated Deprotection of Thiazolidine and Selenazolidine Derivatives Applied to Native Chemical Ligation
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