Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin.
[formula: see text] Isoapoptolidin was isolated from crude fermentation extracts of the apoptolidin-producing microorganism Nocardiopsis sp. Apoptolidin isomerizes to isoapoptolidin upon treatment with methanolic triethylamine to establish a 1.4:1 equilibrium mixture of isoapoptolidin and apoptolidin. Semisynthesis of a peracetylated and deglycosylated derivative of apoptolidin is also described.
Pennington
James D
JD
Department of Chemistry, Texas A&M University, College Station, Texas 77842, USA.
Williams
Howard J
HJ
Salomon
Arthur R
AR
Sulikowski
Gary A
GA
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D004355:Drug Stability; D005285:Fermentation; D006031:Glycosylation; D020128:Inhibitory Concentration 50; D007536:Isomerism; D018942:Macrolides; D025261:Mitochondrial Proton-Translocating ATPases / Q000037:antagonists & inhibitors; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D018942:Macrolides; D025261:Mitochondrial Proton-Translocating ATPases; C114125:apoptolidin