Publications by Jean-Yves Wach

Chemistry and Biology of Natural Products : Applications in Cancer and Infectious Diseases

This thesis is divided in four independent parts related to four different research projects. Each chapter describes one of the multiple aspects covered by organic chemistry, such as the generation of functional interfaces, understanding of biological proc ...

EPFL2011

The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport

Karl Gademann, Jean-Yves Wach

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

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

Simone Bonazzi, Karl Gademann, Jean-Yves Wach, 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

Synthetic Studies on the Sporolides: Exploration of the Enediyne Route

Massimo Binaghi, Simone Bonazzi, Cindy Fellay, Karl Gademann, Jean-Yves Wach

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

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

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

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

Combining Devices and Drugs by Synthetic Natural Product Hybrids

Simone Bonazzi, Karl Gademann, Jean-Yves Wach

2007