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Stratmann K , Burgoyne DL , Moore RE , Patterson GML , Smith CD
Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug- Resistance Reversing Activity
Journal of Organic Chemistry. 1994 Dec 2;59(24) :7219-7226
AbstractHapalosin (2), a novel cyclic depsipeptide from the blue-green alga (cyanobacterium) Hapalosiphon welwitschii W. and G. S. West (Stigonemataceae), shows MDR-reversing activity. Its structure has been determined to be (3S,4R,8R,9S, 12S)-9- benzyl-4-heptyl-8-hydroxy-12-isopropyl-3,10-dimethyl-1,5-dioxa- 10-azacyclododecane-2,6,11-trione by a combination of spectroscopic and chemical methods. The carbon skeleton of 2 was determined by two-dimensional H-1-H-1 and H-1-C-13 NMR correlation experiments and confirmed by mass spectral analysis. The relative and absolute stereochemistry was determined by coupling constant data and Mosher analysis of 2 and three degradation products obtained from acid hydrolysis of 2.
NotesEnglish Article PV566 J ORG CHEM