Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis

Frank Hahn, Nadine Kandziora, Steffen Friedrich and Peter F. Leadlay
Beilstein J. Org. Chem. 2014, 10, 634–640. https://doi.org/10.3762/bjoc.10.55

Supporting Information

The supporting information provides reaction details, analytical data, and copies of 1H and 13C NMR spectra.

Supporting Information File 1: Procedures.
Format: PDF Size: 912.5 KB Download
Supporting Information File 2: NMR spectra.
Format: PDF Size: 3.0 MB Download

Cite the Following Article

Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis
Frank Hahn, Nadine Kandziora, Steffen Friedrich and Peter F. Leadlay
Beilstein J. Org. Chem. 2014, 10, 634–640. https://doi.org/10.3762/bjoc.10.55

How to Cite

Hahn, F.; Kandziora, N.; Friedrich, S.; Leadlay, P. F. Beilstein J. Org. Chem. 2014, 10, 634–640. doi:10.3762/bjoc.10.55

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.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Roß-Taschner, T.; Derra, S.; Stang, J.; Schlotte, L.; Putratama, A.; Hahn, F. Highly Stereoselective Biocatalytic One-Pot Synthesis of Chiral Saturated Oxygen Heterocycles by Integration of a Biosynthetic Heterocyclase into Multiple-Enzyme Cascades. ACS Catalysis 2024, 14, 13420–13428. doi:10.1021/acscatal.4c03692
  • Hahn, F.; Derra, S.; Hoffmann, J. Synthesis of Biomimetic Thioesters for Studies of Ketoreductase Domains from the Biosynthesis of Cytotoxic Polyketides. Synlett 2023, 35, 1707–1712. doi:10.1055/a-2216-4521
  • Derra, S.; Schlotte, L.; Hahn, F. Suzuki–Miyaura Reaction in the Presence of N-Acetylcysteamine Thioesters Enables Rapid Synthesis of Biomimetic Polyketide Thioester Surrogates for Biosynthetic Studies. Chemistry 2023, 5, 1407–1418. doi:10.3390/chemistry5020096
  • Schnepel, C.; Pérez, L. R.; Yu, Y.; Angelastro, A.; Heath, R. S.; Lubberink, M.; Falcioni, F.; Mulholland, K.; Hayes, M. A.; Turner, N. J.; Flitsch, S. L. Thioester-mediated biocatalytic amide bond synthesis with in situ thiol recycling. Nature Catalysis 2022, 6, 89–99. doi:10.1038/s41929-022-00889-x
  • Barajas, J. F.; McAndrew, R. P.; Thompson, M. G.; Backman, T. W. H.; Pang, B.; de Rond, T.; Pereira, J. H.; Benites, V. T.; Martin, H. G.; Baidoo, E. E. K.; Hillson, N. J.; Adams, P. D.; Keasling, J. D. Structural insights into dehydratase substrate selection for the borrelidin and fluvirucin polyketide synthases. Journal of industrial microbiology & biotechnology 2019, 46, 1225–1235. doi:10.1007/s10295-019-02189-z
  • Tang, M.-C.; Fischer, C. R.; Chari, J. V.; Tan, D.; Suresh, S.; Chu, A.; Miranda, M.; Smith, J. D.; Zhang, Z.; Garg, N. K.; St.Onge, R. P.; Tang, Y. Thioesterase-Catalyzed Aminoacylation and Thiolation of Polyketides in Fungi. Journal of the American Chemical Society 2019, 141, 8198–8206. doi:10.1021/jacs.9b01083
  • Shah, D. D.; You, Y. O.; Cane, D. E. Stereospecific Formation of E- and Z-Disubstituted Double Bonds by Dehydratase Domains from Modules 1 and 2 of the Fostriecin Polyketide Synthase. Journal of the American Chemical Society 2017, 139, 14322–14330. doi:10.1021/jacs.7b08896
  • Franke, J.; Hertweck, C. Biomimetic Thioesters as Probes for Enzymatic Assembly Lines: Synthesis, Applications, and Challenges. Cell chemical biology 2016, 23, 1179–1192. doi:10.1016/j.chembiol.2016.08.014
  • Gündemir-Durmaz, T.; Schmid, F.; Baz, Y. E.; Häusser, A.; Schneider, C.; Bilitewski, U.; Rauhut, G.; Garnier, D.; Baro, A.; Laschat, S. Truncated borrelidin analogues: synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation. Organic & biomolecular chemistry 2016, 14, 8261–8269. doi:10.1039/c6ob01358a
  • Friedrich, S.; Hahn, F. Opportunities for enzyme catalysis in natural product chemistry. Tetrahedron 2015, 71, 1473–1508. doi:10.1016/j.tet.2014.12.026
  • Kandziora, N.; Andexer, J. N.; Moss, S. J.; Wilkinson, B.; Leadlay, P. F.; Hahn, F. Uncovering the origin of Z-configured double bonds in polyketides: intermediate E-double bond formation during borrelidin biosynthesis. Chem. Sci. 2014, 5, 3563–3567. doi:10.1039/c4sc00883a
Other Beilstein-Institut Open Science Activities