Discovery and Total Synthesis of Streptoaminals: Antimicrobial [5, 5]‐Spirohemiaminals from the Combined‐Culture of Streptomyces nigrescens and Tsukamurella pulmonis. Issue 35 (27th July 2016)

• Record Type: Journal Article
• Authors: Sugiyama, Ryosuke; Nishimura, Shinichi; Ozaki, Taro; Asamizu, Shumpei; Onaka, Hiroyasu; Kakeya, Hideaki
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 35(2016)
• Page Start: 10278
• Page End: 10282
• Publication Date: 2016-07-27
• Subjects: antimicrobial activity -- combined-cultures -- natural products -- structure elucidation -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201604126
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A series of lipidic spirohemiaminals, designated streptoaminals, is reported. These were discovered by surveying the unique molecular signatures identified in the mass spectrometry data of the combined‐culture broth of Streptomyces nigrescens HEK616 and Tsukamurella pulmonis TP‐B0596. Mass spectrometry analysis showed that streptoaminals appeared as a cluster of ion peaks, which were separated by 14 mass unit intervals, implying the presence of alkyl chains of different lengths. The chemical structures of these compounds were elucidated by spectroscopic analysis and total synthesis. Streptoaminals with globular structures showed broad antimicrobial activities, whereas the planar structures of the 5‐alkyl‐1, 2, 3, 4‐tetrahydroquinolines found in the same combined‐culture did not. This work shows the application of microbes as reservoirs for a range of chemical scaffolds. Abstract : More than the sum of the parts : New antimicrobials were discovered using two approaches: the combined‐culture method, and molecular signature analysis by mass spectrometry.