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Karl Gademann

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Related publications (49)

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Surface Assembly of Catechol-Functionalized Poly(l-lysine)-graft-poly(ethylene glycol) Copolymer on Titanium Exploiting Combined Electrostatically Driven Self-Organization and Biomimetic Strong Adhesion

Karl Gademann, Cyril Portmann

Nonfouling coatings, based on surface-tethered, hydrophilic polymer chains, have widespread application in areas such as biosensing, medical devices, and biotechnology. Self-organization of polymers is a particularly attractive approach given its simplicit ...

American Chemical Society2010

The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport

Karl Gademann

An in vivo nuclear export assay (immunostaining of Rio2 in HeLa cells) demonstrated that (R)-goniothalamin is an inhibitor of nucleocytoplasmic transport above 500 nM, which was rationalized also by molecular modeling. The cytotoxic styryl lactone natural ...

2010

Spatial isolation favours the divergence in microcystin net production by Microcystis in Ugandan freshwater lakes

Karl Gademann, Cyril Portmann

It is generally agreed that the hepatotoxic microcystins (MCs) are the most abundant toxins produced by cyanobacteria in freshwater. In various freshwater lakes in East Africa MC-producing Microcystis has been reported to dominate the phytoplankton, howeve ...

2010

Genetically encoded betaxanthin-based small-molecular fluorescent reporter for mammalian cells

Karl Gademann, Leo Scheller

We designed and engineered a dye production cassette encoding a heterologous pathway, including human tyrosine hydroxylase and Amanita muscaria 4,5-DOPA dioxygenase, for the biosynthesis of the betaxanthin family of plant and fungal pigments in mammalian c ...

2020

Aza-Annulation Strategies in Alkaloid Total Synthesis

Karl Gademann

This review highlights the synthesis of nitrogen-containing natural products via aza-annulation. Strategic, tactical, and methodological perspectives are discussed, including recent developments such as metal- or organocatalyzed reactions, oxidative or red ...

Georg Thieme Verlag2008

Design of a high-throughput device for screening surface modification protocols

Karl Gademann

The development of new high performance, ultra-thin organic coatings requires a strategy that has to consider a large number of surface treatment variables such as binding moieties, substrate, and adsorption conditions (e.g. temperature, solvent, concentra ...

2010

Occurrence of microcystin-producing cyanobacteria in Ugandan freshwater habitats

Karl Gademann, Cyril Portmann

Microcystins (MCs) are cyclic heptapeptides, which are the most abundant toxins produced by cyanobacteria in freshwater. The phytoplankton of many freshwater lakes in Eastern Africa is dominated by cyanobacteria. Less is known, however, on the occurrence o ...

2010

Connecting C-19 Norditerpenoids to C-20 Diterpenes: Total Syntheses of 6-Hydroxy-5,6-dehydrosugiol, 6-Hydroxysugiol, and Taiwaniaquinone H, and Formal Synthesis of Dichroanone

Rosario Scopelliti, Karl Gademann

Oxidation of the B-ring of abietane derivatives by Sharpless dihydroxylation gave the natural products 6-hydroxy-5,6-dehydrosugiol and 6-hydroxysugiol. Moreover, further oxidation gave a hydroxy dione derivative that provides a synthetic entry into the C-1 ...

2010

A Synthetic Entry into the Taiwaniaquinoids Based on a Biogenetic Hypothesis: Total Synthesis of (-)-Taiwaniaquinone H

Rosario Scopelliti, Karl Gademann

(Chemical Equation Presented) Less carbon: Following a biogenetic proposal, the unusual 6-5-6 carbon skeleton of C19 taiwaniaquinoids was obtained by an intramolecular benzilic acid rearrangement from a C20 precur-sor. A protecting-group-free total synthes ...

2010

Natural Product Hybrids

Karl Gademann

This review highlights several classes of natural product hybrids. First, structural hybrids emanating from different biosynthetic pathways exemplified by the polyketide peptide alkaloid anachelin are discussed. Another class is the so-called functional hy ...

2006

Catechol functionalized polymers and method for preparing them

Karl Gademann

Described are compounds that are capable of forming adlayers, said compounds comprising at least one headgroup A, an optional linker B, a polymer C, a terminal group D and an optionally present crosslinking group R, wherein the headgroup A is a compound of ...

2005

Directed Biosynthesis of Phytotoxic Alkaloids in the Cyanobacterium Nostoc 78-12A

Karl Gademann, Cyril Portmann

Nostocarboline, a chlorinated and N-methylated carbolinium alkaloid, displays potent and selective inhibition of photoautotrophic organisms as well as the malaria parasite Plasmodium falciparum, while showing very low toxicity to bacterial and fungal patho ...

2009

Secondary Metabolites from Cyanobacteria: Complex Structures and Powerful Bioactivities

Karl Gademann, Cyril Portmann

This review presents natural products from cyanobacteria. Several classes of secondary metabolites are highlighted. Toxic metabolites from these prokaryotic photosynthetic organisms include compounds such as microcystin, anatoxin and saxitoxin, which displ ...

2008

Surface modifications based on the cyanobacterial siderophore anachelin: from structure to functional biomaterials design

Karl Gademann, Joanna Kobylinska

This review describes the design, synthesis and evaluation of novel catechol based anchors for surface modification. The anachelin chromophore, the catecholate fragment of the siderophore anachelin from the cyanobacterium Anabaena cylindrica, allows for th ...

Springer Netherlands2009

Synthetic Studies on the Sporolides: Exploration of the Enediyne Route

Karl Gademann, Cindy Fellay

Synthetic studies towards the construction of the cyclopenta[a]indene fragment of the heptacyclic marine metabolite sporolide are reported based on a hypothetical biosynthesis. The key step of this biogenetic proposal includes a Bergman cyclization of an e ...

Georg Thieme Verlag2010

Isolation of Aerucyclamides C and D and Structure Revision of Microcyclamide 7806A: Heterocyclic Ribosomal Peptides from Microcystis aeruginosa PCC 7806 and Their Antiparasite Evaluation

Karl Gademann, Cyril Portmann

Aerucyclamides C and D were isolated from the cyanobacterium Microcystis aeruginosa PCC 7806, and their structures established by NMR spectroscopy and chemical transformation and degradation. Acidic hydrolysis of aerucyclamide C (CF3CO2H, H2O) resulted in ...

2008

New antiplasmodial natural products from cyanobacteria: linking their ecological role to their therapeutic potential

Karl Gademann, Cyril Portmann

Cyanobacteria (blue-green algae) produce many metabolites that are directed towards competing photoautotrophs. Such algicidal compounds might offer new approaches for the selective inhibition of the malaria parasite, Plasmodium falciparum, as this organism ...

2009

The cyanobacterial alkaloid nostocarboline: an inhibitor of acetylcholinesterase and trypsin

Karl Gademann

Preselected cyanobacterial strains (available from culture collections and our own isolates), belonging primarily to the heterocystous cluster, were screened for inhibitors against butyrylcholinesterase. About one-half of the extracts exhibited inhibitory ...

2009

Anguinomycins and Derivatives: Total Syntheses, Modeling, and Biological Evaluation of the Inhibition of Nucleocytoplasmic Transport

Karl Gademann, Ivo Zemp

The preparation of the polyketide natural products anguinomycin C and D is reported based on key steps such as Negishi stereoinversion cross coupling, Jacobsen Cr(III)-catalyzed Hetero Diels−Alder reaction, Evans B-mediated syn-aldol chemistry, and B-alkyl ...

2010

Enantioselective Synthesis of the Sporolide Quinone Acid Fragment

Karl Gademann

The sporolide quinone acid is a key fragment in the biosynthesis of the complex heptacyclic marine metabolite sporolide. We report a concise enantioselective route to this fragment, which is obtained in seven steps with 65% overall yield from trimethoxyben ...

2009