Production of new polyene antibiotics by Streptomyces cellulosae after addition of ethyl (Z)-16-phenylhexadec-9-enoate.
Ethyl (Z)-16-phenylhexadec-9-enoate (3), an analog of ethyl oleate (2), was synthesized and added to cultures of Streptomyces cellulosae ATCC 12625 which normally produce fungichromin (1) as the principal polyene antibiotic. These cultures showed drastic reduction of fungichromin biosynthesis but afforded four new polyene antibiotics with a truncated four carbon side chain which are designated as isochainin (11) (an isomer of chainin (10], 14-hydroxyisochainin (12), 1'-hydroxyisochainin (13), and 1',14-dihydroxyisochainin (14). The close correspondence of 13C NMR chemical shifts between these compounds and fungichromin suggests that the stereochemistry at every site is exactly analogous.
Li
Z
Z
Department of Chemistry, University of Alberta, Edmonton, Canada.
Rawlings
B J
BJ
Harrison
P H
PH
Vederas
J C
JC
D000900:Anti-Bacterial Agents / Q000032:analysis / Q000096:biosynthesis*; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis / Q000494:pharmacology*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011090:Polyenes / Q000032:analysis / Q000096:biosynthesis; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013302:Streptomyces / Q000187:drug effects / Q000378:metabolism*
D000900:Anti-Bacterial Agents; D005229:Fatty Acids, Monounsaturated; D011090:Polyenes; C059955:ethyl 16-phenylhexadec-9-enoate