Li Z, Rawlings B J, Harrison P H, Vederas J C
Department of Chemistry, University of Alberta, Edmonton, Canada.
J Antibiot (Tokyo). 1989 Apr;42(4):577-84. doi: 10.7164/antibiotics.42.577.
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.
（Z）-16-苯基十六碳-9-烯酸乙酯（3）是油酸乙酯（2）的类似物，已被合成并添加到纤维素链霉菌ATCC 12625的培养物中，该菌株通常产生真菌色素（1）作为主要的多烯抗生素。这些培养物显示真菌色素生物合成急剧减少，但产生了四种新的多烯抗生素，其具有截短的四个碳的侧链，分别被命名为异链菌素（11）（链菌素（10）的异构体）、14-羟基异链菌素（12）、1'-羟基异链菌素（13）和1'，14-二羟基异链菌素（14）。这些化合物与真菌色素之间的碳-13核磁共振化学位移的密切对应表明每个位点的立体化学完全相似。
