Supporting Information
Experimental details of culture conditions, gene cloning, protein purification, incubation experiments, isolation of 5 and HPLC purifications, the amino acid sequence of BbS, a phylogenetic tree with the location of BbS, SDS-PAGE analysis, listed NMR data of 5, labelling experiments for NMR assignment, synthetic procedures for the NPPs, Mosher ester analysis of epoxides, and chiral GC analysis of nerolidols.
| Supporting Information File 1: Experimental part. | ||
| Format: PDF | Size: 1.3 MB | Download |
Cite the Following Article
Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum
Jan Rinkel and Jeroen S. Dickschat
Beilstein J. Org. Chem. 2019, 15, 789–794.
https://doi.org/10.3762/bjoc.15.75
How to Cite
Rinkel, J.; Dickschat, J. S. Beilstein J. Org. Chem. 2019, 15, 789–794. doi:10.3762/bjoc.15.75
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Presentation Graphic
| Picture with graphical abstract, title and authors for social media postings and presentations. | ||
| Format: PNG | Size: 151.2 KB | Download |
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Zhi, Y.; Dai, C.; Fang, X.; Xiao, X.; Lu, H.; Chen, F.; Chen, R.; Ma, W.; Deng, Z.; Lu, L.; Liu, T. Gene-Directed In Vitro Mining Uncovers the Insect-Repellent Constituent from Mugwort (Artemisia argyi). Journal of the American Chemical Society 2024, 146, 30883–30892. doi:10.1021/jacs.4c08857
- Triningsih, D. W.; Yoshizaki, N.; Igarashi, Y. Wychimicins E and F from a rare actinomycete of the genus Cryptosporangium. The Journal of antibiotics 2024. doi:10.1038/s41429-024-00770-y
- Dickschat, J. S.; Quan, Z.; Schnakenburg, G. A Case of Convergent Evolution: The Bacterial Sesquiterpene Synthase for 1-epi-Cubenol from Nonomuraea coxensis. Chembiochem : a European journal of chemical biology 2023, 24, e202300581. doi:10.1002/cbic.202300581
- Liu, J.; Yao, G.; Wan, X.; Wang, F.; Han, P.; Bao, S.; Wang, K.; Song, T.; Jiang, H. Highly Efficient Biosynthesis of γ-Bisabolene with a New Sesquiterpene Synthase AcTPS5 by Dual Cytoplasmic-Peroxisomal Engineering in Saccharomyces cerevisiae. Fermentation 2023, 9, 779. doi:10.3390/fermentation9090779
- Moreira, V. M. doi:10.1002/9781119608288.ch6
- Hewage, R. T.; Tseng, C.-C.; Liang, S.-Y.; Lai, C.-Y.; Lin, H.-C. Genome mining of cryptic bisabolenes that were biosynthesized by intramembrane terpene synthases from Antrodia cinnamomea. Philosophical transactions of the Royal Society of London. Series B, Biological sciences 2023, 378, 20220033. doi:10.1098/rstb.2022.0033
- Kreuzenbeck, N. B.; Seibel, E.; Schwitalla, J. W.; Fricke, J.; Conlon, B. H.; Schmidt, S.; Hammerbacher, A.; Köllner, T. G.; Poulsen, M.; Hoffmeister, D.; Beemelmanns, C. Comparative Genomic and Metabolomic Analysis of Termitomyces Species Provides Insights into the Terpenome of the Fungal Cultivar and the Characteristic Odor of the Fungus Garden of Macrotermes natalensis Termites. mSystems 2022, 7, e0121421. doi:10.1128/msystems.01214-21
- Hou, A.; Dickschat, J. S. Using Terpene Synthase Plasticity in Catalysis: On the Enzymatic Conversion of Synthetic Farnesyl Diphosphate Analogues. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 15644–15649. doi:10.1002/chem.202103049
- Schotte, C.; Lukat, P.; Deuschmann, A.; Blankenfeldt, W.; Cox, R. J. Untersuchungen zum Verständnis und zur Kontrolle der Stereoselektivität der Humulen-Synthase. Angewandte Chemie 2021, 133, 20470–20475. doi:10.1002/ange.202106718
- Schotte, C.; Lukat, P.; Deuschmann, A.; Blankenfeldt, W.; Cox, R. J. Understanding and Engineering the Stereoselectivity of Humulene Synthase. Angewandte Chemie (International ed. in English) 2021, 60, 20308–20312. doi:10.1002/anie.202106718
- Xu, H.; Rinkel, J.; Dickschat, J. S. Isoishwarane synthase from Streptomyces lincolnensis. Organic Chemistry Frontiers 2021, 8, 1177–1184. doi:10.1039/d0qo01583k
- Lauterbach, L.; Dickschat, J. S. Sesquiterpene synthases for bungoene, pentalenene and epi-isozizaene from Streptomyces bungoensis. Organic & biomolecular chemistry 2020, 18, 4547–4550. doi:10.1039/d0ob00606h
- Rinkel, J.; Köllner, T. G.; Chen, F.; Dickschat, J. S. Characterisation of three terpene synthases for β-barbatene, β-araneosene and nephthenol from social amoebae. Chemical communications (Cambridge, England) 2019, 55, 13255–13258. doi:10.1039/c9cc07681f
- Rinkel, J.; Dickschat, J. S. Mechanistic investigations on multiproduct β-himachalene synthase from Cryptosporangium arvum. Beilstein journal of organic chemistry 2019, 15, 1008–1019. doi:10.3762/bjoc.15.99
