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Karl Gademann

Cette personne n’est plus à l’EPFL

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Publications associées (49)

The First Meeting for Young Chemistry Faculty, Organized by the "Platform Chemistry" of the Swiss Academy of Science (SCNAT)

Karl Gademann

2009

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

Joanna Kobylinska, Karl Gademann, Jean-Yves Wach, Tom Woods

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

Enantioselective Synthesis of the Sporolide Quinone Acid Fragment

Karl Gademann, Jean-Yves Wach

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

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

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

Karl Gademann, Cora Prestinari, Cyril Portmann, Theresa Myers

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

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

Total Synthesis and Neuritotrophic Activity of Farinosone C and Derivatives

Karl Gademann, Henning Jessen

An efficient synthesis of all four possible stereoisomers of the neurotrophic amide farinosone C was developed. The absolute and relative configuration was assigned by comparison of synthetic material with a derivatized authentic sample of the natural prod ...

2009

Antimalarial natural products of marine and freshwater origin

Joanna Kobylinska, Karl Gademann

This review highlights recently discovered antimalarial natural products from marine and freshwater sources described in the literature from 2006 to 2008. The structures as well as bioactivities of compounds against the malaria parasites such as Plasmodium ...

2009

Protein-Resistant Surfaces through Mild Dopamine Surface Functionalization

Simone Bonazzi, Karl Gademann, Jean-Yves Wach

The synthesis and evaluation of new dopamine-based catechol anchors coupled to poly(ethylene glycol) (PEG) for surface modification of TiO2 are reported. Dopamine is modified by dimethylamine-methylene or trimethylammonium- methylene groups, and the prepar ...

2008

Aza-Annulation Strategies in Alkaloid Total Synthesis

Adrien Keith Lawrence, 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

Aerucyclamides A and B: Isolation and Synthesis of Toxic Ribosomal Heterocyclic Peptides from the Cyanobacterium Microcystis aeruginosa PCC 7806

Karl Gademann, Cyril Portmann

Two new modified hexacyclopeptides, aerucyclamides A and B, were isolated from the toxic freshwater cyanobacterium Microcystis aeruginosa PCC 7806. The constitution was assigned by spectroscopic methods, and the configuration determined by chemical degrada ...

2008

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

Stable ß-Turns of Tripeptides in Water through Cation-π Interactions

Karl Gademann

Taking a a turn. Short tripeptides that form stable ß turns in water are remarkably stable against chemical and thermal degradation. Terminal cation-π interactions lead to stabilization of these turns that are formed independently of sequence. ...

2008

Potent and Selective Antiplasmodial Activity of the Cyanobacterial Alkaloid Nostocarboline and its Dimers

Karl Gademann

The quaternary β-carbolinium alkaloid nostocarboline from the cyanobacterium Nostoc 78-12A and ten bis-cationic dimeric derivatives were evaluated against four protozoan parasites and low micromolar values against Trypanosoma brucei, submicromolar values a ...

2008

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

Isolation and Structure Determination of Two Microcystins and Sequence Comparison of the McyABC Adenylation Domains in Planktothrix Species

Karl Gademann, Cyril Portmann

Microcystins (MCs) are toxic heptapeptides found in cyanobacteria and share the common structure cyclo(-D-Ala1-L- X2-D-isoMeAsp3-L-Z4-Adda5-D-isoGlu6-Mdha7). The letters X and Z in the general formula above represent a wide range of L-amino acids that occu ...

2008

Antimicrobial Surfaces through Natural Product Hybrids

Simone Bonazzi, Karl Gademann, Jean-Yves Wach

The power of two! A natural product hybrid (see structure) composed of a siderophore and an antibiotic separated by a poly(ethylene glycol) linker enables the preparation of antimicrobial and cell-resistant surfaces by a simple dip-and-rinse procedure. The ...

Wiley-VCH Verlag GmbH2008

To live and let die in The Big Blue

Karl Gademann

Harmful algal blooms in both freshwater and marine environments pose significant challenges for humans, livestock and aquatic food webs. Over the last 50 years, several authors proposed that small mol. iron chelators (siderophores) could be responsible for ...

American Chemical Society2008

Biomimetic Total Synthesis and Antimicrobial Evaluation of Anachelin H

Karl Gademann

The first biomimetic total synthesis of the iron chelator anachelin H isolated from the cyanobacterium Anabaena cylindrica is reported. A first generation approach delivered one enantiomeric series of the polyketide fragment. Comparison of the 1H NMR data ...

2007

Surface active poly(ethylene glycol) (PEG) catechol derivatives on metal oxide surfaces: influence of pH, pKa and isoelectric point on adsorption kinetics and adlayer stability

Karl Gademann

2007

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