Preparation of new alkyne-modified ansamitocins by mutasynthesis

Kirsten Harmrolfs, Lena Mancuso, Binia Drung, Florenz Sasse and Andreas Kirschning
Beilstein J. Org. Chem. 2014, 10, 535–543. https://doi.org/10.3762/bjoc.10.49

Supporting Information

The supporting information provide the synthesis of building blocks, mutasynthetic experiments as well as purification protocols after fermentations, a short description of the cell proliferation assay, analytical descriptions of new metabolites and copies of 1H and 13C NMR spectra.

Supporting Information File 1: Additional experimental details and NMR spectra.
Format: PDF Size: 788.6 KB Download

Cite the Following Article

Preparation of new alkyne-modified ansamitocins by mutasynthesis
Kirsten Harmrolfs, Lena Mancuso, Binia Drung, Florenz Sasse and Andreas Kirschning
Beilstein J. Org. Chem. 2014, 10, 535–543. https://doi.org/10.3762/bjoc.10.49

How to Cite

Harmrolfs, K.; Mancuso, L.; Drung, B.; Sasse, F.; Kirschning, A. Beilstein J. Org. Chem. 2014, 10, 535–543. doi:10.3762/bjoc.10.49

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

  • Skrzypczak, N.; Buczkowski, A.; Bohusz, W.; Nowak, E.; Tokarska, K.; Leśniewska, A.; Alzebari, A. M.; Ruszkowski, P.; Gdaniec, M.; Bartl, F.; Przybylski, P. Modifications of geldanamycin via CuAAC altering affinity to chaperone protein Hsp90 and cytotoxicity. European journal of medicinal chemistry 2023, 256, 115450. doi:10.1016/j.ejmech.2023.115450
  • Skrzypczak, N.; Przybylski, P. Structural diversity and biological relevance of benzenoid and atypical ansamycins and their congeners. Natural product reports 2022, 39, 1678–1704. doi:10.1039/d2np00004k
  • Bergueiro, J.; Glitscher, E. A.; Calderón, M. A hybrid thermoresponsive plasmonic nanogel designed for NIR-mediated chemotherapy. Biomaterials advances 2022, 137, 212842. doi:10.1016/j.bioadv.2022.212842
  • Sundar, K.; Prabu, T. R. Microbial metabolites in nutrition and healthcare. Volatiles and Metabolites of Microbes; Elsevier, 2021; pp 235–256. doi:10.1016/b978-0-12-824523-1.00012-2
  • Skrzypczak, N.; Pyta, K.; Ruszkowski, P.; Mikołajczak, P.; Kucinska, M.; Murias, M.; Gdaniec, M.; Bartl, F.; Przybylski, P. Anticancer activity and toxicity of new quaternary ammonium geldanamycin derivative salts and their mixtures with potentiators. Journal of enzyme inhibition and medicinal chemistry 2021, 36, 1898–1904. doi:10.1080/14756366.2021.1960829
  • Wesemann, F.; Heutling, A.; Wienecke, P.; Kirschning, A. First Ring-Expanded Maytansin Lactone Accessed by a New Mutasynthetic Variant. Chembiochem : a European journal of chemical biology 2020, 21, 2927–2930. doi:10.1002/cbic.202000336
  • Padilla-Salinas, R.; Sun, L.; Anderson, R.; Yang, X.; Zhang, S.; Chen, Z. J.; Yin, H. Discovery of Small-Molecule Cyclic GMP-AMP Synthase Inhibitors. The Journal of organic chemistry 2020, 85, 1579–1600. doi:10.1021/acs.joc.9b02666
  • Porterfield, W. B.; Zhang, W. Mutasynthesis for Natural Product Bioengineering. Comprehensive Natural Products III; Elsevier, 2020; pp 336–351. doi:10.1016/b978-0-12-409547-2.14633-5
  • Klahn, P.; Fetz, V.; Ritter, A.; Collisi, W.; Hinkelmann, B.; Arnold, T.; Tegge, W.; Rox, K.; Hüttel, S.; Mohr, K. I.; Wink, J.; Stadler, M.; Wissing, J.; Jänsch, L.; Brönstrup, M. The nuclear export inhibitor aminoratjadone is a potent effector in extracellular-targeted drug conjugates. Chemical science 2019, 10, 5197–5210. doi:10.1039/c8sc05542d
  • Dehimat, Z. I.; Yaşar, S.; Tebbani, D.; Özdemir, İ. Sonogashira cross-coupling reaction catalyzed by N-heterocyclic carbene-Pd(II)-PPh3 complexes under copper free and aerobic conditions. Inorganica Chimica Acta 2018, 469, 325–334. doi:10.1016/j.ica.2017.09.048
  • de Cassia Pessotti, R.; Caraballo-Rodríguez, A. M.; Ortega-Domínguez, H. E.; Pupo, M. T.; Newman, D. J.; Cragg, G. M.; Grothaus, P. G. Terrestrial Microbial Natural Products Discovery Guided by Symbiotic Interactions and Revealed by Advanced Analytical Methods. Chemical Biology of Natural Products; CRC Press, 2017; pp 161–188. doi:10.1201/9781315117089-5
  • Devkule, S.; Chavan, S. Copper(I) complexes of N -(2-quinolynylmethylene)-1 H -benzimidazole and triphenylphosphine: Synthesis, characterization, luminescence and catalytic properties. Inorganica Chimica Acta 2017, 466, 122–129. doi:10.1016/j.ica.2017.05.076
  • Classen, T.; Pietruszka, J. Complex molecules, clever solutions – Enzymatic approaches towards natural product and active agent syntheses. Bioorganic & medicinal chemistry 2017, 26, 1285–1303. doi:10.1016/j.bmc.2017.06.045
  • Lin, J.; Zhong, J.-J. Proteomic studies on anti-tumor agent ansamitocin P-3 producer Actinosynnema pretiosum in response to ammonium and isobutanol. Bioprocess and biosystems engineering 2017, 40, 1133–1139. doi:10.1007/s00449-017-1763-5
  • Dewan, A.; Sarmah, M.; Bora, U.; Thakur, A. J. A green protocol for ligand, copper and base free Sonogashira cross-coupling reaction. Tetrahedron Letters 2016, 57, 3760–3763. doi:10.1016/j.tetlet.2016.07.021
  • Pošta, M.; Soós, V.; Beier, P. Design of photoaffinity labeling probes derived from 3,4,5-trimethylfuran-2(5H)-one for mode of action elucidation. Tetrahedron 2016, 72, 3809–3817. doi:10.1016/j.tet.2016.03.096
  • Boecker, S.; Zobel, S.; Meyer, V.; Süssmuth, R. D. Rational biosynthetic approaches for the production of new-to-nature compounds in fungi. Fungal genetics and biology : FG & B 2016, 89, 89–101. doi:10.1016/j.fgb.2016.02.003
  • Lehmann, J.; Wright, M. H.; Sieber, S. A. Making a Long Journey Short: Alkyne Functionalization of Natural Product Scaffolds. Chemistry (Weinheim an der Bergstrasse, Germany) 2016, 22, 4666–4678. doi:10.1002/chem.201504419
  • Bułyszko, I.; Dräger, G.; Klenge, A.; Kirschning, A. Evaluation of the Synthetic Potential of an AHBA Knockout Mutant of the Rifamycin Producer Amycolatopsis mediterranei. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 19231–19242. doi:10.1002/chem.201503548
  • Song, Y. N.; Jiao, R. H.; Zhang, W. J.; Zhao, G. Y.; Dou, H.; Jiang, R.; Zhang, A. H.; Hou, Y. Y.; Bi, S. F.; Ge, H. M.; Tan, R.-X. New ansamycin derivatives generated by simultaneous mutasynthesis. Organic letters 2015, 17, 556–559. doi:10.1021/ol5035639

Patents

  • GÉRARD BAUDOUIN; SHIZUKA MANAMI; MILLER MICHAEL LOUIS; SILVA RICHARD A. METHODS OF PREPARING CYTOTOXIC BENZODIAZEPINE DERIVATIVES. EP 4163284 A1, April 12, 2023.
  • GÉRARD BAUDOUIN; SHIZUKA MANAMI; MILLER MICHAEL LOUIS; SILVA RICHARD A. METHODS OF PREPARING CYTOTOXIC BENZODIAZEPINE DERIVATIVES. EP 3778602 A1, Feb 17, 2021.
  • JAIN NARESHKUMAR; GHONE SANJEEVANI; SMITH SEAN; GLASSFORD IAN; DEGRADO SYLVIA J; KANG FU-AN; ZHAO SENZHI. Cytotoxic agents and conjugates thereof. US 10654873 B2, May 19, 2020.
Other Beilstein-Institut Open Science Activities