Metabolic products of microorganisms. 258. Enzymatic bromination of nikkomycin Z.
Two brominated nikkomycins were produced by enzymatic halogenation of nikkomycin Z in the presence of a nonheme bromoperoxidase isolated from Streptomyces aureofaciens Tü 24. The monobrominated and dibrominated nikkomycin Z derivatives were substituted at the hydroxypyridyl moiety of the N-terminal amino acid of nikkomycin Z at position C-6"' (ZBr) or C-4"' and C-6"' (ZBr2). The brominated nikkomycin Z derivatives had a decreased affinity to chitin synthase of Coprinus cinereus as compared to nikkomycin Z and exhibited a low inhibitory activity towards various fungi and yeasts.
Decker
H
H
Biologisches Institut, Universität Tübingen, Germany.
Pfefferle
U
U
Bormann
C
C
Zähner
H
H
Fiedler
H P
HP
Van Pée
K H
KH
Rieck
M
M
König
W A
WA
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D000935:Antifungal Agents / Q000378:metabolism*; D001419:Bacteria / Q000187:drug effects; D002687:Chitin Synthase / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003001:Cloning, Molecular; D003302:Coprinus / Q000201:enzymology; D015964:Gene Expression Regulation, Bacterial; D015971:Gene Expression Regulation, Enzymologic; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010544:Peroxidases / Q000235:genetics / Q000378:metabolism*; D010957:Plasmids; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013056:Spectrophotometry, Ultraviolet; D013302:Streptomyces / Q000235:genetics; D013304:Streptomyces aureofaciens / Q000201:enzymology*; D014169:Transformation, Bacterial
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; C011952:nikkomycin; D010544:Peroxidases; C026195:bromide peroxidase; D002687:Chitin Synthase