Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst

Autor:	Aaron B Hinds, Wyatt C Powell, Maciej A. Walczak, Siddhartha Akasapu
Rok vydání:	2018
Předmět:	010405 organic chemistry Longest linear sequence Thiazoline Total synthesis General Chemistry Picolinic acid 010402 general chemistry Antimicrobial 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Chemistry chemistry Pyridine Thiazole
Zdroj:	Chemical Science
ISSN:	2041-6520
Popis:	Total synthesis of two thiopeptide antibiotics, micrococcin P1 and thiocillin I, is described featuring new molybdenum catalyst. Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(vi)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C–H activation strategy to install the trisubstituted pyridine core and thiazole groups. The synthetic material displays promising antimicrobial properties measured against a series of Gram-positive bacteria.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9c83aaae8e40889b27b22717f429215f https://pubmed.ncbi.nlm.nih.gov/30881626 Zobrazit plný text záznamu