title: Long-Chain Alkyl Cyanides: Unprecedented Volatile Compounds Released by Pseudomonas and Micromonospora Bacteria.
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.
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.|Laboratório de Semioquímicos, Departamento de Química-UFPR, Curitiba, PR, Brazil.
authors.forename: Diogo
authors.initials: D
authors.lastname: Montes Vidal
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Anna-Lena
authors.initials: AL
authors.lastname: von Rymon-Lipinski
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Srinivasa
authors.initials: S
authors.lastname: Ravella
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Ulrike
authors.initials: U
authors.lastname: Groenhagen
authors.affiliation: Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, Saarland University, Saarbrücken, Germany.
authors.forename: Jennifer
authors.initials: J
authors.lastname: Herrmann
authors.affiliation: Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, Saarland University, Saarbrücken, Germany.
authors.forename: Nestor
authors.initials: N
authors.lastname: Zaburannyi
authors.affiliation: Laboratório de Semioquímicos, Departamento de Química-UFPR, Curitiba, PR, Brazil.
authors.forename: Paulo H G
authors.initials: PH
authors.lastname: Zarbin
authors.affiliation: SIB Swiss Institute of Bioinformatics, Switzerland.
authors.forename: Adithi R
authors.initials: AR
authors.lastname: Varadarajan
authors.affiliation: SIB Swiss Institute of Bioinformatics, Switzerland.
authors.forename: Christian H
authors.initials: CH
authors.lastname: Ahrens
authors.affiliation: Institute for Viticulture and Oenology, University of Applied Sciences and Arts Western Switzerland, Switzerland.|Agroscope, Switzerland.
authors.forename: Laure
authors.initials: L
authors.lastname: Weisskopf
authors.affiliation: Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, Saarland University, Saarbrücken, Germany.
authors.forename: Rolf
authors.initials: R
authors.lastname: Müller
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Stefan
authors.identifier: 0000-0002-4810-324X
authors.initials: S
authors.lastname: Schulz
mesh_terms: D008847:Micromonospora / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000032:analysis* / Q000138:chemical synthesis; D011549:Pseudomonas / Q000737:chemistry*; D055549:Volatile Organic Compounds / Q000032:analysis* / Q000138:chemical synthesis
chemical_list: D009570:Nitriles; D055549:Volatile Organic Compounds
keywords: antibiotics; biosynthesis; fatty acids; isotopic labeling; nitriles