Long-Chain Alkyl Cyanides: Unprecedented Volatile Compounds Released by Pseudomonas and Micromonospora Bacteria

  • Angew Chem Int Ed Engl. 2017 Apr 3;56(15):4342-4346. doi: 10.1002/anie.201611940.
Diogo Montes Vidal  1  2 ,  Anna-Lena von Rymon-Lipinski  1 ,  Srinivasa Ravella  1 ,  Ulrike Groenhagen  1 ,  Jennifer Herrmann  3 ,  Nestor Zaburannyi  3 ,  Paulo H G Zarbin  2 ,  Adithi R Varadarajan  4 ,  Christian H Ahrens  4 ,  Laure Weisskopf  5  6 ,  Rolf Müller  3 ,  Stefan Schulz  1
Affiliations
  • 1. Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
  • 2. Laboratório de Semioquímicos, Departamento de Química-UFPR, Curitiba, PR, Brazil.
  • 3. Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, Saarland University, Saarbrücken, Germany.
  • 4. SIB Swiss Institute of Bioinformatics, Switzerland.
  • 5. Institute for Viticulture and Oenology, University of Applied Sciences and Arts Western Switzerland, Switzerland.
  • 6. Agroscope, Switzerland.
PMID: 28276609 DOI: 10.1002/anie.201611940
Abstract

The analysis of volatiles from Bacterial cultures revealed long-chain aliphatic nitriles, a new class of natural products. Such nitriles are produced by both Gram-positive Micromonospora echinospora and Gram-negative Pseudomonas veronii bacteria, although the structures differ. A variable sequence of chain elongation and dehydration in the fatty acid biosynthesis leads to either unbranched saturated or unsaturated nitriles with an ω-7 double bond, such as (Z)-11-octadecenenitrile, or methyl-branched unsaturated nitriles with the double bond located at C-3, such as (Z)-13-methyltetradec-3-enenitrile. The nitrile biosynthesis starts from fatty acids, which are converted into their amides and finally dehydrated. The structures and biosyntheses of the 19 naturally occurring compounds were elucidated by mass spectrometry, synthesis, and feeding experiments with deuterium-labeled precursors. Some of the nitriles showed antimicrobial activity, for example, against multiresistant Staphylococcus aureus strains.

Keywords
antibiotics; biosynthesis; fatty acids; isotopic labeling; nitriles.
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