Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity

Klemens Stratmann, David L. Burgoyne, Richard E. Moore, Gregory M.L. Patterson, Charles D. Smith

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Abstract

Hapalosin (2), a novel cyclic depsipeptide from the blue-green alga (cyanobacterium) Hapalosiphon welwitschii W. & G. S. West (Stigonemataceae), shows MDR-reversing activity. Its structure has been determined to be (3S,4S,8S,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 1H— and 1H—13C 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.

Original languageEnglish (US)
Pages (from-to)7219-7226
Number of pages8
JournalJournal of Organic Chemistry
Volume59
Issue number24
DOIs
StatePublished - Dec 1 1994

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Stratmann, K., Burgoyne, D. L., Moore, R. E., Patterson, G. M. L., & Smith, C. D. (1994). Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity. Journal of Organic Chemistry, 59(24), 7219-7226. https://doi.org/10.1021/jo00103a011