Structure and Biosynthesis of Isatropolones, Bioactive Amine‐Scavenging Fluorescent Natural Products from Streptomyces Gö66. Issue 18 (30th March 2017)

• Record Type: Journal Article
• Authors: Cai, Xiaofeng; Shi, Yi‐Ming; Pöhlmann, Nicole; Revermann, Ole; Bahner, Isabel; Pidot, Sacha J.; Wesche, Frank; Lackner, Helmut; Büchel, Claudia; Kaiser, Marcel; Richter, Christian; Schwalbe, Harald; Stinear, Timothy P.; Zeeck, Axel; Bode, Helge B.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 18(2017)
• Page Start: 4945
• Page End: 4949
• Publication Date: 2017-03-30
• Subjects: 1, 5-diketones -- fluorescence -- isatropolones -- natural products -- rubrolones; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201701223
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The natural products isatropolone A–C (1 –3 ) were reisolated from Streptomyces Gö66, with1 and3 showing potent activity against Leishmania donovani. They contain a rare tropolone ring derived from a type II polyketide biosynthesis pathway. Their biosynthesis was elucidated by labeling experiments, analysis of the biosynthesis gene cluster, its partial heterologous expression, and structural characterization of various intermediates. Owing to their 1, 5‐diketone moiety, they can react with ammonia, amines, lysine, and lysine‐containing peptides and proteins, which results in the formation of a covalent bond and subsequent pyridine ring formation. Their fluorescence properties change upon amine binding, enabling the simple visualization of reacted amines including proteins. Abstract : A good green catch ! The structure and biosynthesis of the isatropolone natural products are described. These compounds show a dramatic change in fluorescence upon binding to amines and amine‐containing peptides and proteins.