Structure elucidation of Sch 20561, a cyclic dehydropeptide lactone--a major component of W-10 antifungal antibiotic.
Antibiotic W-10 is a fermentation complex produced by the bacterium Aeromonas sp. W-10. The cyclic dehydropeptide lactones Sch 20562 (1) and Sch 20561 (2) are the major components of this fermentation complex and are of biological interest in view of their unique structural features and potent antifungal activity. The chemical degradation studies that were utilized in the assignment of structure 2 for Sch 20561 are described here. The structure determination of 2 made use of the ozonolytic cleavage of the dehydropeptide units to form fragments that were sequenced by mass spectrometry. The cyclic dehydropeptide lactone Sch 20561 (2) was found to be the aglycone of Sch 20562 (1) and these two natural products were correlated by a chemical transformation involving the deglucosidation of 1 to form 2.
Afonso
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Department of Chemistry, Schering-Plough Research Institute, Kenilworth, New Jersey 07033, USA.
Hon
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Brambilla
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D000333:Aeromonas / Q000737:chemistry*; D000596:Amino Acids / Q000032:analysis; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry*; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D005285:Fermentation; D008401:Gas Chromatography-Mass Spectrometry; D007783:Lactones / Q000737:chemistry; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D010126:Ozone / Q000737:chemistry; D010455:Peptides; D010456:Peptides, Cyclic / Q000737:chemistry*; D010504:Periodic Acid / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D007783:Lactones; D018942:Macrolides; D010455:Peptides; D010456:Peptides, Cyclic; C120181:Sch 20561; D010504:Periodic Acid; D010126:Ozone; C009288:metaperiodate; D015032:Zinc