Structure of the new spiroketal-macrolide A82548A.
A new member of the spiroketal-containing macrolide class of fermentation-derived natural products was isolated from mycelial extracts of Streptomyces diastatochromogenes. The principal component, A82548A, was shown to possess a 22-membered macrolide ring system onto which was incorporated both a spiroketal and a hemiketal moiety. Relative stereochemistry was established by single crystal X-ray diffraction studies. Absolute stereochemistry was determined via hydrolysis of the amino sugar glycosidically linked to the aglycone, which was identified as L-kedarosamine. The overall three-dimensional structure is closely related to that of the macrolides cytovaricin, rutamycin, and ossamycin.
Kirst
H A
HA
Lilly Research Laboratories, Greenfield, Indiana 46140, USA.
Larsen
S H
SH
Paschal
J W
JW
Occolowitz
J L
JL
Creemer
L C
LC
Steiner
J L
JL
Lobkovsky
E
E
Clardy
J
J
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification*; D018360:Crystallography, X-Ray; D005285:Fermentation; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013302:Streptomyces
C096633:A 82548A; D000900:Anti-Bacterial Agents; D018942:Macrolides; D013141:Spiro Compounds; C033385:cytovaricin