Ryu, C.-M. et al. Bacterial volatiles promote growth in arabidopsis. Proc. Natl Acad. Sci. USA 100, 4927–4932 (2003).
Article CAS PubMed PubMed Central Google Scholar
Lee, H. H., Molla, M. N., Cantor, C. R. & Collins, J. J. Bacterial charity work leads to population-wide resistance. Nature 467, 82–86 (2010).
Article CAS PubMed PubMed Central Google Scholar
Chernin, L. et al. Quorum-sensing quenching by rhizobacterial volatiles. Environ. Microbiol. Rep. 3, 698–704 (2011).
Article CAS PubMed Google Scholar
Vespermann, A., Kai, M. & Piechulla, B. Rhizobacterial volatiles affect the growth of fungi and Arabidopsis thaliana. Appl. Environ. Microbiol. 73, 5639–5641 (2007).
Article CAS PubMed PubMed Central Google Scholar
von Reuss, S. H., Kai, M., Piechulla, B. & Francke, W. Octamethylbicyclo[3.2.1]octadienes from the rhizobacterium Serratia odorifera. Angew. Chem. Int. Ed. 49, 2009–2010 (2010).
Domik, D., Magnus, N. & Piechulla, B. Analysis of a new cluster of genes involved in the synthesis of the unique volatile organic compound sodorifen of Serratia plymuthica 4Rx13. FEMS Microbiol. Lett. 363, fnw139 (2016).
Domik, D. et al. A terpene synthase is involved in the synthesis of the volatile organic compound sodorifen of Serratia plymuthica 4Rx13. Front. Microbiol. 7, 737 (2016).
Article PubMed PubMed Central Google Scholar
von Reuss, S. et al. Sodorifen biosynthesis in the rhizobacterium Serratia plymuthica involves methylation and cyclization of MEP-derived farnesyl pyrophosphate by a SAM-dependent C-methyltransferase. J. Am. Chem. Soc. 140, 11855–11862 (2018).
Duell, E. R. et al. Direct pathway cloning of the sodorifen biosynthetic gene cluster and recombinant generation of its product in E. coli. Microb. Cell. Fact. 18, 32 (2019).
Article PubMed PubMed Central Google Scholar
Rabe, P. et al. Conformational analysis, thermal rearrangement and EI-MS-fragmentation mechanism of (1(10)E,4E,6S,7R)-germacradien-6-ol by 13C-labeling experiments. Angew. Chem. Int. Ed. 54, 13448–13451 (2015).
Eustaquio, A. S., Pojer, F., Noel, J. P. & Moore, B. S. Discovery and characterization of a marine bacterial SAM-dependent chlorinase. Nat. Chem. Biol. 4, 69–74 (2008).
Article CAS PubMed Google Scholar
Rabe, P. et al. Terpene cyclases from social amoebae. Angew. Chem. Int. Ed. 55, 15420–15423 (2016).
Rabe, P. et al. Mechanistic investigantions on two bacterial diterpene cyclases: spiroviolene synthase and tsukubadiene synthase. Angew. Chem. Int. Ed. 56, 2776–2779 (2017).
Rinkel, J. & Dickschat, J. S. Addressing the chemistry of germacrene A by isotope labeling experiments. Org. Lett. 21, 2426–2429 (2019).
Article CAS PubMed Google Scholar
Rinkel, J., Lauterbach, L., Rabe, P. & Dickschat, J. S. Two diterpene synthases for spiroalbatene and cembrene A from Allokutzneria albata. Angew. Chem. Int. Ed. 57, 3238–3241 (2018).
Cornforth, J. W., Cornforth, R. H., Donninger, C. & Popjak, G. Studies on the biosynthesis of cholesterol XIX. Steric course of hydrogen eliminations and of C–C bond formations in squalene biosynthesis. Proc. R. Soc. London, Ser. B 163, 492–514 (1966).
Rinkel, J. et al. Mechanisms of the diterpene cyclases β-pinacene synthase from Dictyostelium discoideum and hydropyrene synthase from Streptomyces clavuligerus. Chem. Eur. J. 23, 10501–10505 (2017).
Article CAS PubMed Google Scholar
Reetz, M. T. Dytropic rearrangements, a new class of orbital-symmetry controlled reactions. Type I. Angew. Chem. Int. Ed. 11, 129–130 (1972).
Hugelshofer, C. L. & Magauer, T. Dyotropic rearrangements in natural product total synthesis and biosynthesis. Nat. Prod. Rep. 34, 228–234 (2017).
Article CAS PubMed Google Scholar
Gutierrez, O. & Tantillo, D. J. Analogies between synthetic and biosynthetic reactions in which [1,2]-alkyl shifts are combined with other events: dyotropic, Schmidt, and carbocation rearrangements. J. Org. Chem. 77, 8845–8850 (2012).
Article CAS PubMed Google Scholar
Li, H. & Dickschat, J. S. Isotopic labelling experiments and enzymatic preparation of iso-casbenes with casbene synthase from Ricinus communis. Org. Chem. Front. 9, 795–801 (2022).
Mitsuhashi, T., Rinkel, J., Okada, M., Abe, I. & Dickschat, J. S. Mechanistic characterization of two chimeric sesterterpene synthases from Penicillium. Chem. Eur. J. 23, 10053–10057 (2017).
Article CAS PubMed Google Scholar
Cornforth, J. W., Cornforth, R. H., Popjak, G. & Yengoyan, L. Studies on the biosynthesis of cholesterol XX. Steric course of decarboxylation of 5-pyrophosphomevalonate and of the carbon to carbon bond formation in the biosynthesis of farnesyl pyrophosphate. J. Biol. Chem. 241, 3970–3987 (1966).
Article CAS PubMed Google Scholar
Adamo, C. & Barone, V. Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: the mPW and mPW1PW models. J. Chem. Phys. 108, 664–675 (1998).
Matsuda, S. P. T., Wilson, W. K. & Xiong, Q. Mechanistic insights into triterpene synthesis from quantum mechanical calculations. Detection of systematic errors in B3LYP cyclization energies. Org. Biomol. Chem. 4, 530–543 (2006).
Article CAS PubMed Google Scholar
Hong, Y. J. & Tantillo, D. J. A maze of dyotropic rearrangements and triple shifts: carbocation rearrangements connecting stemarene, stemodene, betaerdene, aphidicolene, and scopadulanol. J. Org. Chem. 83, 3780–3793 (2018).
Article CAS PubMed Google Scholar
Quan, Z., Hou, A., Goldfuss, B. & Dickschat, J. S. Mechanism of the bifunctional multiple product sesterterpene synthase AcAS from Aspergillus calidoustus. Angew. Chem. Int. Ed. 61, e202117273 (2022).
Lemfack, M. C. et al. Reaction mechanism of the farnesyl pyrophosphate C-methyltransferase towards the biosynthesis of pre-sodorifen pyrophosphate by Serratia plymuthica 4Rx13. Sci. Rep. 11, 3182 (2021).
Article CAS PubMed PubMed Central Google Scholar
Burger, U., Delay, A. & Mazenod, F. 1,2,3,4,5-Pentamethyl-5-acetyl-cyclopentadien-1,3, ein ungewöhnliches Keton. Helv. Chim. Acta 57, 2106–2111 (1974).
Pace, V. et al. Efficient access to all-carbon quaternary and tertiary α-functionalized homoallyl-type aldehydes from ketones. Angew. Chem. Int. Ed. 56, 12677–12682 (2017).
Dess, D. B. & Martin, J. C. Readily accessible 12-I-51 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem. 48, 4155–4156 (1983).
Horner, L., Hoffmann, H., Wippel, H. G. & Klahre, G. Phosphinoxyde als olefiniemgsreagenzien. Chem. Ber. 92, 2499–2505 (1959).
Wadsworth, W. S. & Emmons, W. D. The utility of phosphonate carbanions in olefin synthesis. J. Am. Chem. Soc. 83, 1733–1738 (1961).
Wise, M. L., Savage, T. J., Katahira, E. & Croteau, R. Monoterpene synthases from common sage (Salvia officinalis): cDNA Isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineol synthase, and (+)-bornyl diphosphate synthase. J. Biol. Chem. 273, 14891–14899 (1998).
Article CAS PubMed Google Scholar
Nakano, C., Kim, H.-K. & Ohnishi, Y. Identification of the first bacterial monoterpene cyclase, a 1,8-cineole synthase, that catalyzes the direct conversion of geranyl diphosphate. ChemBioChem 12, 1988–1991 (2011).
Article CAS PubMed Google Scholar
Jamieson, C. S., Ohashi, M., Liu, F., Tang, Y. & Houk, K. N. The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery. Nat. Prod. Rep. 36, 698–713 (2019).
Article CAS PubMed PubMed Central Google Scholar
Zhang, B. et al. Enzyme-catalysed [6 + 4] cycloadditions in the biosynthesis of natural products. Nature 568, 122–126 (2019).
Article CAS PubMed PubMed Central Google Scholar
Harmata, M. The (4 + 3)-cycloaddition reaction: simple allylic cations as dienophiles. Chem. Commun. 46, 8886–8903 (2010).
Giets, R. D. & Schiestl, R. H. High-efficiency yeast transformation using the LiAc/SS carrier DNA/PEG method. Nat. Protoc. 2, 31–34 (2007).
留言 (0)