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!

Publications

Beemelmanns C, Nitsch D, Bentz C, Reissig HU (2019) Stereoselective Cascade Cyclizations with Samarium Diiodide to Tetracyclic Indolines - Precursors of Fluorostrychnines and Brucine. Chemistry - European Journal [Accepted] Details PubMed

Leichnitz D, Pflanze S, Beemelmanns C (2019) Stereoselective Synthesis of Unnatural (2S,3S)-6-Hydroxy-4-Sphingenine-Containing Sphingolipids Org Bio Chem [Accepted] Details Open Access

Raguz L, Beemelmanns C (2019) Ursprung und Funktionen der Sphingolipide Nachrichten aus der Chemie 67(2), 66-70. (Review) Details PubMed Code

Rischer M, Raguz L, Guo H, Keiff F, Diekert G, Goris T, Beemelmanns C (2018) Biosynthesis, Synthesis and Activities of Barnesin A, a NRPS-PKS Hybrid Produced by an Anaerobic Epsilonproteobacterium ACS Chem Biol 13(8), 1990-1995. Details PubMed

Leichnitz D, Raguž L, Beemelmanns C (2017) Total synthesis and functional analysis of microbial signalling molecules. Chem Soc Rev 46(20), 6330-6344. (Review) Details PubMed

Rischer M, Leichnitz D, Beemelmanns C (2017) Bakterien-induzierte Morphogenese mariner Eukaryoten Wissenschaft BIOSpektrum 2017(6), 634-637. (Review) Details Open Access Code

Cantley AM, Woznica A, Beemelmanns C, King N, Clardy J (2016) Isolation and Synthesis of a Bacterially Produced Inhibitor of Rosette Development in Choanoflagellates. J Am Chem Soc 138(13), 4326-4329. Details PubMed

Woznica A, Cantley AM, Beemelmanns C, Freinkman E, Clardy J, King N (2016) Bacterial lipids activate, synergize, and inhibit a developmental switch in choanoflagellates. Proc Natl Acad Sci U S A 113(28), 7894-7899. Details PubMed

Beemelmanns C, Reissig H.-U. (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. Details PubMed

Beemelmanns C, Reissig H.-U. (2015) Strychnine as Target - Samarium Diiodide as Tool - A Personal Story The Chemical Record 15(5), 872-885. Details PubMed

Beemelmanns C, Woznica A, Alegado RA, Cantley AM, King N, Clardy J (2014) Synthesis of the rosette-inducing factor RIF-1 and analogs. J. Am. Chem. Soc. 136(29), 10210-10213. Details PubMed

Staff

Dr. Christine Beemelmanns

Head

Phone: +49 3641 532-1525 Email: christine.beemelmanns@leibniz-hki.de

Daniel Leichnitz

PhD student

Phone: +49 3641 532-1501 Email: daniel.leichnitz@leibniz-hki.de

Luka Raguž

PhD student

Phone: +49 3641 532-1523 Email: luka.raguz@leibniz-hki.de

David Roman

PhD student

Phone: +49 3641 532-1525 Email: david.roman@leibniz-hki.de