Rational reprogramming of the sesquiterpene synthase BcBOT2 yields new terpenes with presilphiperfolane skeleton

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Vanessa Nikolaiczyk
  • Jenny Irwan
  • Trang Nguyen
  • Jörg Fohrer
  • Philipp Elbers
  • Paul Schrank
  • Mehdi D. Davari
  • Andreas Kirschning

Organisationseinheiten

Externe Organisationen

  • Leibniz-Institut für Pflanzenbiochemie, Halle (IPB)
  • Technische Universität Darmstadt
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Details

OriginalspracheEnglisch
Seiten (von - bis)233-244
Seitenumfang12
FachzeitschriftCatalysis Science and Technology
Jahrgang13
Ausgabenummer1
PublikationsstatusVeröffentlicht - 24 Nov. 2022

Abstract

Computer-aided rational design of the substrate binding pocket of sesquiterpene synthases BcBOT2 from Botrytis cinerea yielded FPP cyclization products with presilphiperfolane backbone other than the naturally formed sesquiterpene presilphiperfolan-8β-ol. Particularly, amino acids W118 and F138 were found to strongly control the stability and conformation of key cationic intermediates. The W118Q variant forms only presilphiperfolan-9β-ol, whereas the exchange of amino acids at position 138, such as F138V, has a fundamental effect on the course of the cationic cascade. Here, the 1,3-hydride shift en route to presilphiperfolan-8β-ol is suppressed and substituted by a so far unknown 1,2-hydride shift that leads to presilphiperfol-1-ene and presilphiperfolan-1α-ol along with β-caryophyllene and the so far unknown caryophyllene-8β-ol.

ASJC Scopus Sachgebiete

  • Chemische Verfahrenstechnik (insg.)
  • Katalyse

Zitieren

Rational reprogramming of the sesquiterpene synthase BcBOT2 yields new terpenes with presilphiperfolane skeleton. / Nikolaiczyk, Vanessa; Irwan, Jenny; Nguyen, Trang et al.
in: Catalysis Science and Technology, Jahrgang 13, Nr. 1, 24.11.2022, S. 233-244.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Nikolaiczyk V, Irwan J, Nguyen T, Fohrer J, Elbers P, Schrank P et al. Rational reprogramming of the sesquiterpene synthase BcBOT2 yields new terpenes with presilphiperfolane skeleton. Catalysis Science and Technology. 2022 Nov 24;13(1):233-244. doi: 10.1039/d2cy01617f
Nikolaiczyk, Vanessa ; Irwan, Jenny ; Nguyen, Trang et al. / Rational reprogramming of the sesquiterpene synthase BcBOT2 yields new terpenes with presilphiperfolane skeleton. in: Catalysis Science and Technology. 2022 ; Jahrgang 13, Nr. 1. S. 233-244.
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abstract = "Computer-aided rational design of the substrate binding pocket of sesquiterpene synthases BcBOT2 from Botrytis cinerea yielded FPP cyclization products with presilphiperfolane backbone other than the naturally formed sesquiterpene presilphiperfolan-8β-ol. Particularly, amino acids W118 and F138 were found to strongly control the stability and conformation of key cationic intermediates. The W118Q variant forms only presilphiperfolan-9β-ol, whereas the exchange of amino acids at position 138, such as F138V, has a fundamental effect on the course of the cationic cascade. Here, the 1,3-hydride shift en route to presilphiperfolan-8β-ol is suppressed and substituted by a so far unknown 1,2-hydride shift that leads to presilphiperfol-1-ene and presilphiperfolan-1α-ol along with β-caryophyllene and the so far unknown caryophyllene-8β-ol.",
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AU - Nikolaiczyk, Vanessa

AU - Irwan, Jenny

AU - Nguyen, Trang

AU - Fohrer, Jörg

AU - Elbers, Philipp

AU - Schrank, Paul

AU - Davari, Mehdi D.

AU - Kirschning, Andreas

N1 - Funding Information: We thank Dr. Gerald Dräger (Leibniz Universität Hannover, Hannover, Germany) for excellent support in the structural analysis of MS spectrometric data. MDD is supported through funds from IPB Halle.

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N2 - Computer-aided rational design of the substrate binding pocket of sesquiterpene synthases BcBOT2 from Botrytis cinerea yielded FPP cyclization products with presilphiperfolane backbone other than the naturally formed sesquiterpene presilphiperfolan-8β-ol. Particularly, amino acids W118 and F138 were found to strongly control the stability and conformation of key cationic intermediates. The W118Q variant forms only presilphiperfolan-9β-ol, whereas the exchange of amino acids at position 138, such as F138V, has a fundamental effect on the course of the cationic cascade. Here, the 1,3-hydride shift en route to presilphiperfolan-8β-ol is suppressed and substituted by a so far unknown 1,2-hydride shift that leads to presilphiperfol-1-ene and presilphiperfolan-1α-ol along with β-caryophyllene and the so far unknown caryophyllene-8β-ol.

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