752251-08-4Relevant articles and documents
Biomimetic total synthesis and antimicrobial evaluation of anachelin H
Gademann, Karl,Bethuel, Yann,Locher, Hans H.,Hubschwerlen, Christian
, p. 8361 - 8370 (2008/09/18)
(Chemical Equation Presented) 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 suggested the relative configuration of this anachelin fragment. The relative and absolute configuration of anachelin H was then established by total synthesis. A second generation approach involved the enzymatic conversion of N,N-dimethyltyramine to the anachelin chromophore. It was demonstrated that the enzyme tyrosinase is activated by the product during this reaction, the anachelin chromophore can serve as a tyrosinase activator. Anachelin H was evaluated against a panel of eleven bacterial and fungal pathogens, and moderate antibiotic activity (32 μg/mL) against Moraxella catarrhalis was found.
Stereoselective total synthesis of (-)-galantinic acid
Bethuel, Yann,Gademann, Karl
, p. 1580 - 1582 (2007/10/03)
A concise, practical and stereoselective total synthesis of galantinic acid, constituent of the peptide antibiotic galantin, is reported. The title compound is obtained in six steps via Heathcock-Claisen condensation, Evans reduction and deprotection in 1
A biomimetic route to the peptide alkaloid anachelin
Gademann, Karl,Bethuel, Yann
, p. 3327 - 3329 (2007/10/03)
A postulated biogenesis forms the basis for a synthetic route to the natural product anachelin H (1). Key steps include a tellurium-mediated, oxidative aza annulation and a Claisen condensation under mild conditions. Experiments with a model substrate ind
