Synthesis of Biotinylated Galiellalactone Analogues

Synthesis of Biotinylated Galiellalactone Analogues

Two biotinylated derivatives of the fungal metabolite galiellalactone (1) were synthesized in order to facilitate the investigation of the molecular mechanism of action of the galiellalactonoids. Galiellalactone is a STAT3-signaling inhibitor that inhibits growth in vitro as well as in vivo of prostate cancer cells expressing activated STAT3. To provide a suitable point of attachment for biotin...

Diastereoselective Total Synthesis of (-)-Galiellalactone.

An enantioselective total synthesis of (-)-galiellalactone has been accomplished. The key features of the synthesis involve the highly stereoselective construction of the cis-trisubstituted cyclopentane intermediate by a Pd(0)-catalyzed cyclization, the stereospecific introduction of an angular hydroxyl group by Riley oxidation, and the efficient construction of the tricyclic system of (-)-gali...

Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide.

A biotinylated heparosan hexasaccharide was synthesized using a one-pot multi-enzyme strategy, in situ activation and transfer of N-trifluoroacetylglucosamine (GlcNTFA) to a heparin backbone significantly improved the synthetic efficiency. The biotinylated hexasaccharide could serve as a flexible core to diversify its conversion into heparan sulfate isoforms with potential biological applicatio...

Chemical Synthesis of Nucleoside Analogues Chemical Synthesis of Nucleoside Analogues

ATTEMPTED SYNTHESIS OF QUINONEMETHINE DERIVATIVE OF NOCARDICIN A ANALOGUES

The synthesis of some 13-lactams is described. 'The electronic activation of monocyclic B-lactams provided by a quinonemethine function was found to instabilize the 13-lactam ring toward nucleophilic: attack by water