The Structure of Hormaomycin and One of Its All-Peptide Aza-Analogues in Solution: Syntheses and Biological Activities of New Hormaomycin Analogues
✍ Scribed by Uwe M. Reinscheid; Boris D. Zlatopolskiy; Christian Griesinger; Axel Zeeck; Armin de Meijere
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Volume
- 11
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
Four new aza‐analogues of hormaomycin 1, a secondary metabolite with interesting biological activities produced by Streptomyces griseoflavus, were synthesized and subjected to preliminary tests of their antibiotic activity to provide new insights into the structure–activity relationship studies of this class of compounds. The solution structures of hormaomycin 1 and its aza‐analogue 2 a were determined by NMR spectroscopy. The data exhibited a reasonably rigid conformation for both molecules, stabilized by stacking interactions between the aromatic moieties attached to the ring and the side chain. According to NMR‐spectral data the aza‐analogue epi‐2 a has a rather different conformation and indeed shows no antibacterial activity whatsoever.