Synthesis of capuramycin and its analogues via a Ferrier-type I reaction and their biological evaluation. (1st November 2022)

• Record Type: Journal Article
• Authors: Kusaka, Shintaro; Yamamoto, Kazuki; Shinohara, Motoko; Minato, Yusuke; Ichikawa, Satoshi
• Is Part Of: Bioorganic & medicinal chemistry. Volume 73(2022)
• Publication Date: 2022-11-01
• Subjects: Antibacterial -- Natural product -- Nucleoside -- MraY -- Structure-activity relationship; TB tuberculosis -- MraY phospho-MurNAc-pentapeptide translocase; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2022.117011
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: To create your abstract, type over the instructions in the template box below. Abstract: The total synthesis of capuramycin (1 ), which is a promising anti-tubercular antibiotics, has been accomplished using Ferrier-type I reaction as a key step. This total synthesis is an alternative approach to the synthesis of capuramycin and its analogues. The 3′- O -demethyl analogue (2 ), which exhibits an equivalent antibacterial activity as capuramycin (1 ) against Mycobacterium smegmatis and Mycobacterium avium, is suggested to have potential as a lead structure of capuramycin analogues because 2 is more accessible from a synthetic view point.