Structural elucidation of trace components combining GC/MS, GC/IR, DFT-calculation and synthesis-salinilactones, unprecedented bicyclic lactones from Salinispora bacteria

TitleStructural elucidation of trace components combining GC/MS, GC/IR, DFT-calculation and synthesis-salinilactones, unprecedented bicyclic lactones from Salinispora bacteria
Publication TypeJournal Article
Year of Publication2018
AuthorsSchlawis C., Kern S., Kudo Y., Grunenberg J., Moore BS, Schulz S.
Volume57
Pagination14921-14925
Date Published2018/11
Type of ArticleArticle
ISBN Number1433-7851
Accession NumberWOS:000452234400043
KeywordsA-factor; autoinducer; bicyclic lactones; biosynthesis; chemistry; efficient; gamma-butyrolactone; GC/IR; growth; identification; morphological development; secondary metabolism; streptomyces-griseus; structure elucidation; volatiles
Abstract

The analysis of volatiles released by marine Salinispora bacteria uncovered a new class of natural compounds displaying an unusual bicyclic [3.1.0]-lactone skeleton. Although only sub-mu g quantities of the compounds were available, the combination of analytical methods, computational spectroscopy, and synthesis allowed unambiguous structural identification of the compounds, called salinilactones, without the need for isolation. Orthogonal hyphenated methods, GC/MS and solid-phase GC/IR allowed to propose a small set of structures consistent with the data. A candidate structure was selected by comparison of DFT-calculated IR spectra and the experimental IR-spectrum. Synthesis confirmed the structure and absolute configuration of three bicyclic lactones, salinilactones A-C. The salinilactones are structurally closely related to the A-factor class of compounds, autoregulators from streptomycete bacteria. They exhibited inhibitory activity against Salinispora and Streptomyces strains.

DOI10.1002/anie.201807923
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