Structure and biosynthesis of FD-594; a new antitumor antibiotic.
The structure of a novel antitumor antibiotics FD-594 (1), produced by Streptomyces sp. TA-0256, was determined to have a glycosylated pyrano[4',3':6,7]naphtho[1,2-b]-xanthene skeleton by means of spectral data. The biosynthetic studies of the chromophore of 1 was also carried out by feeding experiments with [1-13C]-, [2-13C]-, and [1,2-13C2]sodium acetate. The labeling pattern was determined by 13C NMR including 2D INADEQUATE experiments, which allowed us to elucidate that the chromophore of 1 is derived from 14 acetate, followed by the loss of one carbon atom.
Kondo
K
K
Department of Chemistry, Tokyo Institute of Technology, Japan.
Eguchi
T
T
Kakinuma
K
K
Mizoue
K
K
Qiao
Y F
YF
D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011714:Pyrans / Q000737:chemistry*; D013302:Streptomyces / Q000378:metabolism*; D014966:Xanthenes / Q000737:chemistry*
D000903:Antibiotics, Antineoplastic; C112184:FD 594, antibiotic; D011714:Pyrans; D014966:Xanthenes