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- Title
Total Synthesis of Nucleoside Antibiotics Amicetin, Plicacetin, and Cytosaminomycin A—D.
- Authors
Fu, Jiqiang Please verify that the linked ORCID identifiers are correct for each author. The ORCID ID for 'Biao Yu' seems to be invalid. Please check and supply the correct ORCID ID. --> Please confirm that given names and surnames/family names have been iden; Xu, Peng; Yu, Biao
- Abstract
Main observation and conclusion: Amicetin and congeners constitute a small family of complex pyrimidine nucleosides, which exhibit strong antibiotic activities against Gram‐positive bacteria and notably against strains of Mycobacterium tuberculosis. Herein, we report chemical synthesis of a series of disaccharide congeners of the amicetin family, including amicetin, plicacetin, and cytosaminomycin A—D. It is the first time for successful synthesis of amicetin, the prototypical member, and cytosaminomycins. The synthetic approach employs glycosyl N‐phenyltrifluoroacetimidate and thioglycoside donors to construct the characteristic aminodeoxydisaccharides consisting of α‐(1→4)‐glycosidic linkage, uses gold(I)‐catalyzed N‐glycosylation to furnish 2‐deoxy‐β‐nucleosides, and finally exploits amidation and global deprotection to complete the syntheses. It is noteworthy that the 3‐O‐protecting group in the 2‐deoxydisaccharide donors is found to be crucial for a successful N‐glycosylation to assemble the cytosaminomycin disaccharide nucleosides.
- Subjects
ANTIBIOTIC synthesis; NUCLEOSIDE synthesis; PYRIMIDINE nucleosides; ANTIBIOTICS; CHEMICAL synthesis; MYCOBACTERIUM tuberculosis
- Publication
Chinese Journal of Chemistry, 2021, Vol 39, Issue 10, p2679
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202100284