TY - JOUR
T1 - Structural Elucidation of Trace Components Combining GC/MS, GC/IR, DFT-Calculation and Synthesis—Salinilactones, Unprecedented Bicyclic Lactones from Salinispora Bacteria
AU - Schlawis, Christian
AU - Kern, Simone
AU - Kudo, Yuta
AU - Grunenberg, Jörg
AU - Moore, Bradley S.
AU - Schulz, Stefan
N1 - Funding Information:
This work was supported by NIH grant GM085770 to B.S.M. and a JSPS Overseas Research Fellowships postdoctoral fellowship from the Japan Society for Promotion of Science to Y.K. The authors thank Prof. Paul Jensen, Scripps Institution of Oceanography in La Jolla, for the Salinispora strains and cultivation advice and Prof. Joachim Wink, Helmholtz Centre for Infection Research in Braunschweig, for advice regarding the cultivation of Streptomycetes and the provision of streptomycete bacteria.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/11/5
Y1 - 2018/11/5
N2 - 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-μg 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.
AB - 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-μg 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.
KW - A-factor
KW - GC/IR
KW - autoinducer
KW - bicyclic lactones
KW - structure elucidation
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U2 - 10.1002/anie.201807923
DO - 10.1002/anie.201807923
M3 - Article
C2 - 30199596
AN - SCOPUS:85055021049
VL - 57
SP - 14921
EP - 14925
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 45
ER -