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The Structure of Hormaomycin and One of Its All‐Peptide Aza‐Analogues in Solution: Syntheses and Biological Activities of New Hormaomycin Analogues
Author(s) -
Reinscheid Uwe M.,
Zlatopolskiy Boris D.,
Griesinger Christian,
Zeeck Axel,
de Meijere Armin
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400977
Subject(s) - chemistry , stereochemistry , molecule , peptide , stacking , ring (chemistry) , nuclear magnetic resonance spectroscopy , biological activity , streptomyces , side chain , antibacterial activity , metabolite , combinatorial chemistry , organic chemistry , bacteria , biochemistry , biology , in vitro , polymer , genetics
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.