| Title: | Long-Chain Alkyl Cyanides: Unprecedented Volatile Compounds Released by Pseudomonas and Micromonospora Bacteria |
| Author(s): | Montes Vidal D; von Rymon-Lipinski AL; Ravella S; Groenhagen U; Herrmann J; Zaburannyi N; Zarbin PH; Varadarajan AR; Ahrens CH; Weisskopf L; Muller R; Schulz S; |
| Address: | "Institut fur Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany. Laboratorio de Semioquimicos, Departamento de Quimica-UFPR, Curitiba, PR, Brazil. Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, Saarland University, Saarbrucken, Germany. SIB Swiss Institute of Bioinformatics, Switzerland. Institute for Viticulture and Oenology, University of Applied Sciences and Arts Western Switzerland, Switzerland. Agroscope, Switzerland" |
| ISSN/ISBN: | 1521-3773 (Electronic) 1433-7851 (Linking) |
| 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 omega-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: | Micromonospora/*chemistry Molecular Structure Nitriles/*analysis/chemical synthesis Pseudomonas/*chemistry Volatile Organic Compounds/*analysis/chemical synthesis antibiotics biosynthesis fatty acids isotopic labeling nitriles; |
| Notes: | "MedlineMontes Vidal, Diogo von Rymon-Lipinski, Anna-Lena Ravella, Srinivasa Groenhagen, Ulrike Herrmann, Jennifer Zaburannyi, Nestor Zarbin, Paulo H G Varadarajan, Adithi R Ahrens, Christian H Weisskopf, Laure Muller, Rolf Schulz, Stefan eng Research Support, Non-U.S. Gov't Germany 2017/03/10 Angew Chem Int Ed Engl. 2017 Apr 3; 56(15):4342-4346. doi: 10.1002/anie.201611940. Epub 2017 Mar 9" |
