Structural elucidation of aculeximycin. III. Planar structure of aculeximycin, belonging to a new class of macrolide antibiotics.
The planar structure of aculeximycin (1) produced by Streptosporangium albidum has been determined by spectral methods and chemical degradations such as 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU)-methanol reaction, ozonolysis, and periodative oxidation. The antibiotic consists of a 30-membered polyhydroxy lactone ring, an alpha, beta-unsaturated ester group, an intramolecular hemiketal, an oligosaccharide (aculexitriose), a neutral sugar and an amino sugar. The structure of aculeximycin is closely related to those of sporaviridins produced by Streptosporangium viridogriseum. We consider that aculeximycin and sporaviridins belong to a new class of macrolide antibiotics, which is different from the polyol macrolides produced by Streptomyces.
Murata
H
H
Faculty of Pharmacy, Meijo University, Nagoya, Japan.
Suzuki
K
K
Tabayashi
T
T
Hattori
C
C
Takada
Y
Y
Harada
K
K
Suzuki
M
M
Ikemoto
T
T
Shibuya
T
T
Haneishi
T
T
D000107:Acetylation; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D013237:Stereoisomerism
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D018942:Macrolides; C060470:sporaviridin; C039610:aculeximycin