Biomimetic total synthesis and antimicrobial evaluation of anachelin H.
J Org Chem
; 72(22): 8361-70, 2007 Oct 26.
Article
in En
| MEDLINE
| ID: mdl-17902695
ABSTRACT
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 microg/mL) against Moraxella catarrhalis was found.
Search on Google
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Oligopeptides
/
Quinolinium Compounds
/
Saccharomyces cerevisiae
/
Moraxella catarrhalis
/
Anti-Bacterial Agents
/
Antifungal Agents
Language:
En
Journal:
J Org Chem
Year:
2007
Document type:
Article
Affiliation country:
Switzerland