Natural product synthesis and derivatisation
Many natural products are only produced in minor amounts and a full structural characterization is nearly impossible. In addition, many pharmaceutically interesting compounds are too toxic and need derivatisation to improve their pharmacological properties.
Therefore, we are establishing synthetic strategies towards sphingoid-type natural products and functionalized lipids, which represent important signaling molecules in our ecological mdoel systems.
Synthesis of new NRPS-derived natural products
Based on a comparative genome analysis, we were able to isolate a new natural product - barnesin A. Further bioactivity studies showed that barnesin A is a cysteine protease inhibitor with nanomolar activity. The total synthesis enabled further structural activity studies.
For more details, see Maja's article in ACS ChemBio!
(2020) Stereoselective construction of (E,Z)-1,3-dienes and its application in natural product synthesis. Advanced Synthesis & Catalysis [Accepted] (Review)
(2019) Stereoselective cascade cyclizations with samarium diiodide to tetracyclic indolines - precursors of fluorostrychnines and brucine. Chemistry 25(37), 8780-8789.
(2019) Stereoselective synthesis of unnatural (2S,3S)-6-hydroxy-4-sphingenine-containing sphingolipids. Org Biomol Chem 17(29), 6964-6969.
(2019) Ursprung und Funktionen der Sphingolipide. Nachrichten aus der Chemie 67(2), 66-70. (Review)
(2018) Biosynthesis, synthesis and activities of barnesin A, a NRPS-PKS hybrid produced by an anaerobic Epsilonproteobacterium. ACS Chem Biol 13(8), 1990-1995.
(2017) Total synthesis and functional analysis of microbial signalling molecules. Chem Soc Rev 46(20), 6330-6344. (Review)
(2017) Bakterien-induzierte Morphogenese mariner Eukaryoten Wissenschaft. BIOSpektrum 2017(6), 634-637. (Review)
(2016) Isolation and Synthesis of a Bacterially Produced Inhibitor of Rosette Development in Choanoflagellates. J Am Chem Soc 138(13), 4326-4329.
(2016) Bacterial lipids activate, synergize, and inhibit a developmental switch in choanoflagellates. Proc Natl Acad Sci U S A 113(28), 7894-7899.
(2015) Evolution of a Short Route to Strychnine by Using the Samarium Diiodide-Induced Cascade Cyclization as a Key Step Chemistry - A European Journal 21(23), 8416-8425.
(2015) Strychnine as Target - Samarium Diiodide as Tool - A Personal Story The Chemical Record 15(5), 872-885.
(2014) Synthesis of the rosette-inducing factor RIF-1 and analogs. J. Am. Chem. Soc. 136(29), 10210-10213.
Dr. Christine Beemelmanns
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