Journal
SCIENCE CHINA-CHEMISTRY
Volume 64, Issue 10, Pages 1736-1742Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-021-1072-6
Keywords
iodination; tiacumicin; metal-free; facile chemistry
Categories
Funding
- Key Science and Technology Project of Hainan Province (Key Science and Technology Project) [ZDKJ202018]
- Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) [2019ZD0406]
- Chinese Academy of Sciences [QYZDJ-SSW-DQC004]
- National Natural Science Foundation of China [81872778, 31630004, 41911530078]
- Ministry of Science and Technology of China [2018YFC1406705]
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A facile and nonenzymatic iodination method for didechlorotiacumicin B was discovered during the study on halide compatibility of TiaM, which also showed compatibility with other 9 aromatic substrates for iodination.
Tiacumicin B (also known as fidaxomicin or difimicin) is a marketed 18-membered macrolide antibiotic for the treatment of Clostridium difficile infections. Tiacumicin B is structurally characterized with two chlorine atoms substituted on the aromatic ring, which is installed by the halogenase TiaM. During the study on halide compatibility of TiaM, a facile and nonenzymatic iodination method of didechlorotiacumicin B was discovered, requiring NaI, acid and air for iodination at room temperature. This method was also amenable to other 9 aromatic substrates with electron-rich sites for iodination.
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