CP-60,993, a new dianemycin-like ionophore produced by Streptomyces hygroscopicus ATCC 39305: fermentation, isolation and characterization.
CP-60,993, 19-epi-dianemycin, is a novel polycyclic ether antibiotic produced by Streptomyces hygroscopicus ATCC 39305. Fermentation recovery, purification and crystallization were achieved using standard procedures. CP-60,993 was characterized as a monocarboxylic acid. Elemental analysis suggested a molecular formula of C47H78O14 for the free acid and C47H77O14 Na for the sodium salt. Crystalline from CP-60,993 sodium salt shows the following properties: m.p. 193-205 degrees C, E1%(1 cm) = 157 at 232 nm, [alpha]25 degrees C(D) + 11.0 (c 1, methanol). The structure, determined by MS, PMR and CMR, differs from dianemycin only in the stereochemistry at position 19. This was confirmed by X-ray crystallography carried out on the rubidium salt of CP-60,993. It exhibited activity in vitro against Gram-positive and anaerobic bacteria, efficacy against Eimeria coccidia in vivo in poultry, and stimulation in vitro of rumen propionic acid production.
Cullen
W P
WP
Central Research, Pfizer Inc., Groton, CT 06340.
Bordner
J
J
Huang
L H
LH
Moshier
P M
PM
Oscarson
J R
JR
Presseau
L A
LA
Ware
R S
RS
Whipple
E B
EB
Kojima
Y
Y
Maeda
H
H
D000617:Aminoglycosides; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003460:Crystallization; D004539:Eimeria / Q000187:drug effects*; D005285:Fermentation; D008401:Gas Chromatography-Mass Spectrometry; D007476:Ionophores / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D012988:Soil Microbiology; D013302:Streptomyces / Q000378:metabolism*; D014961:X-Ray Diffraction
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D007476:Ionophores; C000904:dianemycin