Schnelle chemische Charakterisierung bakterieller Terpen‐ Synthasen

Rabe, Patrick; Dickschat, Jeroen S.

doi:10.1002/ange.201209103

Cited by 26 publications

(4 citation statements)

References 29 publications

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“…The putative sesquiterpene synthases were functionally characterized by GC/MS analysis of the volatile components of the headspace from recombinant BL21(DE3) E. coli cultures. [46,47] Predicted 1,6-and 1,10-cyclizing sesquiterpene synthases produce bisabolyl cation and putative (Z,E)-germacradienylcation-derived terpenes…”

Section: S Hirsutum Produces a Wide Range Of Sesquiterpenesmentioning

confidence: 99%

Mushroom Hunting by Using Bioinformatics: Application of a Predictive Framework Facilitates the Selective Identification of Sesquiterpene Synthases in Basidiomycota

et al. 2013

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Basidiomycota represent a diverse source of natural products, particularly the sesquiterpenoids. Recently, the genome sequencing, mining, and subsequent discovery of a suite of sesquiterpene synthases was described in Omphalotus olearius. A predictive framework was developed to facilitate the discovery of sesquiterpene synthases in Basidiomycota. Phylogenetic analyses indicated a conservation of both sequence and initial cyclization mechanisms used. Here, the first robust application of this predictive framework is reported. It is used to pursue and selectively identify sesquiterpene synthases that follow a 1,6-, 1,10-, and 1,11-cyclization mechanism in the crust fungus Stereum hirsutum. The successful identification and characterization of a 1,6- and a 1,10-cyclizing sesquiterpene synthase, as well as three 1,11-cyclizing Δ-6 protoilludene synthases, is described. This study verifies the accuracy and utility of the predictive framework as a roadmap for the discovery of specific sesquiterpene synthases from Basidiomycota, representing an important step forward in natural product discovery.

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Section: S Hirsutum Produces a Wide Range Of Sesquiterpenesmentioning

confidence: 99%

Mushroom Hunting by Using Bioinformatics: Application of a Predictive Framework Facilitates the Selective Identification of Sesquiterpene Synthases in Basidiomycota

et al. 2013

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“…Für unsere detaillierte mechanistische Untersuchung wurde das Gen der Terpencyclase aus dem Actinobakterium Streptomyces pristinaespiralis ATCC 25486 (Zugangsnummer WP 005317515) [17] kloniert und in Escherichia coli exprimiert, gefolgt von der Aufreinigung des Proteins in seiner aktiven Form. Das isolierte Enzym wurde sowohl mit einer Serie natürlicher (Oligo)prenyldiphosphate, einschließlich Dimethylallyl-PP (DMAPP), Geranyl-PP (GPP), Farnesyl-PP (FPP) und Geranylgeranyl-PP (GGPP), wie auch den nichtnatürlichen Substratanaloga (2Z,6E)-FPP, 2-Fluor-FPP (2F-FPP) und DHFPP inkubiert (für die Synthese: Abbildung 1 der Hintergrundinformationen (SI)).…”

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Substratinduzierte Konformationsänderungen in Klasse‐I‐Terpencyclasen

et al. 2014

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Wir präsentieren kristallographische und funktionelle Daten einer ,7(11)-dien-Synthase (SdS) aus Streptomyces pristinaespiralis in offener und geschlossener (Ligand-gebundener) Konformation. Durch Analyse einer Substrat-induzierten Konformationsänderung des G1/2-Helixbruchmotivs wurde ein Induced-Fit-Mechanismus identifiziert. Diese Konformationsänderung hebt eine bis dahin unbeschriebene Effektortriade, bestehend aus dem Pyrophosphat-Sensor Arg178, dem Linker Asp181 und dem Effektor Gly182-O, hervor. Dieses Strukturmotiv ist hoch konserviert in Klasse-I-Terpencyclasen von Bakterien, Pilzen und Pflanzen, einschließlich der epi-Isozizaen-Synthase (3KB9), der Aristolochen-Synthase (4KUX), der Bornyldiphosphat-Synthase (1N20), der Limonen-Synthase (2ONG), der 5-epi-Aristolochen-Synthase (5EAT) und der Taxa-4(5),11(12)-dien-Synthase (3P5R). Strukturbasierte Mutageneseexperimente in Kombination mit der Analyse der Produktspektren stützen die mechanistischen Modelle der Carbokationbildung und -stabilisierung in der SdS.[ + ] Diese Autoren trugen zu gleichen Teilen zu dieser Arbeit bei.[**] Wir danken den Mitarbeitern des PXI vom Paul Scherrer Institut, Swiss Light Source (Villigen, Schweiz) für ihre Hilfe bei der kristallographischen Datenerfassung. Diese Arbeit wurde von der Deutschen Forschungsgemeinschaft (DI1536/2-1 und DI1536/4-1) sowie vom Beilstein-Institut zur Fçrderung der Chemischen Wissenschaften mit einem Promotionsstipendium (an P.R.) gefçrdert.Hintergrundinformationen zu diesem Beitrag sind im WWW unter http://dx.

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“…The terpenes geosmin and methylisoborneol are typical terpenes of the actinomycetes. Various sesquiterpene cyclases occur in the streptomycetes [ 3 , 30 , 32 ] and give rise to a wide variety of sesquiterpenes, in this case valencene.…”

Section: Resultsmentioning

confidence: 99%

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

Groenhagen

Maczka

Dickschat

et al. 2014

Beilstein J. Org. Chem.

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Summary Streptomyces sp. FORM5 is a bacterium that is known to produce the antibiotic streptazolin and related compounds. We investigated the strain for the production of volatiles using the CLSA (closed-loop stripping analysis) method. Liquid and agar plate cultures revealed the formation of new 2-alkylpyridines (streptopyridines), structurally closely related to the already known 2-pentadienylpiperidines. The structures of the streptopyridines A to E were confirmed by total synthesis. The analysis of the liquid phase by solvent extraction or extraction with an Oasis adsorbent showed that streptazolin and 2-pentadienylpiperidine are the major compounds, while the streptopyridines are only minor components. In the gas phase, only the streptopyridines could be detected. Therefore, an orthogonal set of analysis is needed to assess the metabolic profile of bacteria, because volatile compounds are obviously overlooked by traditional analytical methods. The streptopyridines are strain specific volatiles that are accompanied by a broad range of headspace constituents that occur in many actinomycetes. Volatiles might be of ecological importance for the producing organism, and, as biosynthetic intermediates or shunt products, they can be useful as indicators of antibiotic production in a bacterium.

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Schnelle chemische Charakterisierung bakterieller Terpen‐ Synthasen

Cited by 26 publications

References 29 publications

Mushroom Hunting by Using Bioinformatics: Application of a Predictive Framework Facilitates the Selective Identification of Sesquiterpene Synthases in Basidiomycota

Mushroom Hunting by Using Bioinformatics: Application of a Predictive Framework Facilitates the Selective Identification of Sesquiterpene Synthases in Basidiomycota

Substratinduzierte Konformationsänderungen in Klasse‐I‐Terpencyclasen

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

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