Total Synthesis and Bioactivity Profile of (+)-Ieodomycins A and B and their Stereoisomers
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Title
- Total Synthesis and Bioactivity Profile of (+)-Ieodomycins A and B and their Stereoisomers
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Author(s)
- Sung, Dan Bi; Choi, Dubong; Seol, Jae Hee; Kang, Na Lae; Kim, Eun A; Heo, Seong Yeong; Heo, Soo Jin; Lee, Jong Seok
- KIOST Author(s)
- Sung, Dan Bi(성단비); Kang, Na Lae(강나래); Kim, Eun A(김은아); Heo, Seong Yeong(허성영); Heo, Soo Jin(허수진); Lee, Jong Seok(이종석)
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Alternative Author(s)
- 성단비; 최두봉; 설재희; 강나래; 김은아; 허성영; 허수진; 이종석
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Publication Year
- 2024-06
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Abstract
- Herein, we report the first- and second-generation syntheses of (+)-ieodomycins A and B and their stereoisomers via the late-stage elaboration of their conjugated E-diene side chains. Key steps for successful synthesis included Keck asymmetric allylation to introduce a hydroxyl group at the C5 position, consecutive Wipf’s carboalumination modification, iodination, Sharpless asymmetric dihydroxylation, one-carbon homologation via cyanation, Mukaiyama lactonization, and Stille cross-coupling to form the conjugated E-diene moiety. Further, the preliminary in vitro bioactivity profile against various disease-related molecular targets and cell lines was investigated. Results indicated that compounds 30b and 30c, diastereoisomers of (+)-ieodomycin B (2), serve as α-glucosidase inhibitors, while compounds 30b and 30d inhibit the angiotensin-converting enzyme.
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/45693
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DOI
- 10.1021/acsomega.4c03241
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Bibliographic Citation
- ACS Omega, 2024
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Publisher
- ACS Publications
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Type
- Article
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Language
- English
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Document Type
- Article; Early Access
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