title: Structural elucidation of aculeximycin. III. Planar structure of aculeximycin, belonging to a new class of macrolide antibiotics.
abstract: 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.
authors.affiliation: Faculty of Pharmacy, Meijo University, Nagoya, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Murata
authors.forename: K
authors.initials: K
authors.lastname: Suzuki
authors.forename: T
authors.initials: T
authors.lastname: Tabayashi
authors.forename: C
authors.initials: C
authors.lastname: Hattori
authors.forename: Y
authors.initials: Y
authors.lastname: Takada
authors.forename: K
authors.initials: K
authors.lastname: Harada
authors.forename: M
authors.initials: M
authors.lastname: Suzuki
authors.forename: T
authors.initials: T
authors.lastname: Ikemoto
authors.forename: T
authors.initials: T
authors.lastname: Shibuya
authors.forename: T
authors.initials: T
authors.lastname: Haneishi
mesh_terms: 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
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D018942:Macrolides; C060470:sporaviridin; C039610:aculeximycin