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Published on: September 30, 2014
Pneumocandins from Zalerion arboricola. III. Structure elucidation
O D Hensens1, J M Liesch, D L Zink
1Department of Natural Products Chemistry, Merck Research Laboratories, Rahway, N.J. 07065-0900.
Abstract:
Pneumocandin B0 (6) and six related lipopeptides are antifungal and anti-Pneumocystis carinii agents from mutants of Zalerion arboricola, whose structures were determined mainly on the basis of spectroscopic analysis. They belong, along with pneumocandin A0 (L-671,329) previously isolated from these laboratories, to the echinocandin class of antifungal agents. The product from base-catalyzed ring opening involving the hemiaminal position of the dihydroxyornithine residue of B0, has been clearly defined as 6b. Modifications were limited to the 3-hydroxy-4-methylproline, 3,4-dihydroxyhomotyrosine and 4,5-dihydroxyornithine residues of pneumocandin A0.
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