Total Synthesis and Stereochemistry Assignment of Nucleoside Antibiotic A‐94964. (16th February 2022)

• Record Type: Journal Article
• Authors: Shao, Xiaofei; Zheng, Chang; Xu, Peng; Shiraishi, Taro; Kuzuyama, Tomohisa; Molinaro, Antonio; Silipo, Alba; Yu, Biao
• Is Part Of: Angewandte Chemie. Volume 134:Number 14(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-02-16
• Subjects: A-94964 -- Nucleoside Antibiotic -- Octuronic Acid Uridine -- Phosphodiester -- Total Synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202200818
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A collective total synthesis of eight diastereoisomers associated with NMR analysis leads to a full stereochemistry assignment of the structurally unique nucleoside antibiotic A‐94964, which features an octuronic acid uridine core decorated with an α‐D‐mannopyranosyl residue and an α‐D‐ N ‐acylglucosaminopyranosyl residue via a phosphodiester bridge. Abstract : Full stereochemical assignment of the structurally unique nucleoside antibiotic A‐94964, which shows potent inhibitory activity against the vital bacterial phospho‐ N ‐acetylmuramyl‐pentapeptide translocase, was achieved by the collective total synthesis of eight diastereoisomers in combination with NMR analysis.