752251-06-2Relevant academic research and scientific papers
An alternative approach to the synthesis of the three fragments of anachelin H
Gamba-Sánchez, Diego,Garzón-Posse, Fabián,Prunet, Jo?lle
, p. 2702 - 2715 (2020/04/17)
The synthesis of the fully protected peptide, polyketide and alkaloid fragments of anachelin H is presented. The peptide fragment was prepared using a liquid phase peptide synthesis; the polyketide fragment was synthetized using a cross metathesis and an intramolecular oxa-Michael reaction as the key steps to introduce the desired stereochemistry; finally, the alkaloid fragment was obtained by an oxidative cyclization of a catechol derivative using potassium ferricyanide. The synthesis of all fragments was based on the use of natural amino acids as sources of asymmetry. The independent synthesis of the three fragments should allow more efficient biological studies on the fragments instead of the whole natural product. Experiments to illustrate the coupling of fragments and the effectiveness of the convergent strategy are also described.
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.
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
