CP-78,545, a new monocarboxylic acid ionophore antibiotic related to zincophorin and produced by a Streptomyces.
A new monocarboxylic acid ionophore antibiotic related to zincophorin, CP-78,545 (1), was found in the culture broth of Streptomyces sp. N731-45. CP-78,545 was extracted with organic solvents and purified by column chromatography. The metabolite, which is active in vitro against certain Gram-positive bacteria, as well as the anaerobe Treponema hyodysenteriae, and a coccidium Eimeria tenella, was isolated as a water insoluble magnesium salt (2) in 2:1 (ligand/metal) stoichiometry. The structure of CP-78,545 was elucidated by spectroscopic (NMR and MS) methods, and the relative stereochemistry was determined by single-crystal X-ray analysis of the cadmium salt (3). CP-78,545, i.e., 24-dehydrozincophorin, is unique since its molecular backbone contains a terminal double bond previously not found in other polyether ionophores.
Dirlam
J P
JP
Central Research, Pfizer Inc., Groton, CT 06340.
Belton
A M
AM
Chang
S P
SP
Cullen
W P
WP
Huang
L H
LH
Kojima
Y
Y
Maeda
H
H
Nishiyama
S
S
Oscarson
J R
JR
Sakakibara
T
T
D000818:Animals; D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000302:isolation & purification*; D002264:Carboxylic Acids / Q000096:biosynthesis / Q000302:isolation & purification* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002645:Chickens; D003049:Coccidiostats / Q000096:biosynthesis / Q000302:isolation & purification*; D005285:Fermentation; D007476:Ionophores / Q000096:biosynthesis / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013302:Streptomyces / Q000378:metabolism; D014961:X-Ray Diffraction
D000900:Anti-Bacterial Agents; D002264:Carboxylic Acids; D003049:Coccidiostats; D007476:Ionophores; C060645:CP 78545