Discovery and Total Synthesis of Streptoaminals: Antimicrobial [5,5]-Spirohemiaminals from the Combined-Culture of Streptomyces nigrescens and Tsukamurella pulmonis

Ryosuke Sugiyama, Shinichi Nishimura, Taro Ozaki, Shumpei Asamizu, Hiroyasu Onaka, Hideaki Kakeya

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)10278-10282
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number35
DOIs
Publication statusPublished - 2016 Aug 22

Keywords

  • antimicrobial activity
  • combined-cultures
  • natural products
  • structure elucidation
  • total synthesis

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