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PreprintCC BY-NC-NDChemRxiv

Mechanistic characterization of a bacterial terpene synthase that bifurcates to produce both 6/10- and 5/11-bicyclic diterpenes

  • Wenbo Ning1,2
  • Pin-Shuo Huang1,2
  • Xiuting Wei1,2
  • Fabrizio G. Cavassa1,2
  • Jordan Nafie3
  • Jeffrey D. Rudolf1,2
  1. 1Department of Chemistry
  2. 2University of Florida
  3. 3BioTools, Inc., 5730 Corporate Way, Suite 220, West Palm Beach, Florida, 33407
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Abstract

The mechanism of the bacterial diterpene synthase ChtS from Chitinophaga japonensis was investigated. ChtS was found to produce two major diterpenes, 5/11-bicyclic chitino-2,5,9-triene (11) and the previously uncharacterized 6/10-bicyclic chitinoeunicellene (12). Deuterium labeling experiments, site-directed mutagenesis, and isolation of minor products cembrene C (13), cembrene A (14), and chitinol (15) support initial 1,14-cyclization, two sequential 1,2-hydride shifts, prior to bifurcation to 11 or 12, ultimately retaining the E-configured C-2/C-3 alkene.

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Cite

BibTeXRIS
BibTeX
@misc{ning2026mechanistic,
  title = {{Mechanistic characterization of a bacterial terpene synthase that bifurcates to produce both 6/10- and 5/11-bicyclic diterpenes}},
  author = {Wenbo Ning and Pin-Shuo Huang and Xiuting Wei and Fabrizio G. Cavassa and Jordan Nafie and Jeffrey D. Rudolf},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010488/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010488/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Mechanistic characterization of a bacterial terpene synthase that bifurcates to produce both 6/10- and 5/11-bicyclic diterpenes
AU  - Wenbo Ning
AU  - Pin-Shuo Huang
AU  - Xiuting Wei
AU  - Fabrizio G. Cavassa
AU  - Jordan Nafie
AU  - Jeffrey D. Rudolf
PY  - 2026
DA  - 2026/10/14
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010488/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010488/v1
AB  - The mechanism of the bacterial diterpene synthase ChtS from Chitinophaga japonensis was investigated. ChtS was found to produce two major diterpenes, 5/11-bicyclic chitino-2,5,9-triene (11) and the previously uncharacterized 6/10-bicyclic chitinoeunicellene (12). Deuterium labeling experiments, site-directed mutagenesis, and isolation of minor products cembrene C (13), cembrene A (14), and chitinol (15) support initial 1,14-cyclization, two sequential 1,2-hydride shifts, prior to bifurcation to 11 or 12, ultimately retaining the E-configured C-2/C-3 alkene.
ER  -