Absolute configurations of macrolide antibiotics of the bafilomycin and leucanicidin groups

O’Shea M., Rickards R.W., Rotheschild J.M. and Lacey E.

The Journal of Antibiotics, 1997, 50, 1073-1077.

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Antibiotics of the bafilomycin and leucanicidin groups isolated from various microorganisms of the order actintomycetales have been known for some years to possess a broad spectrum of biological activity against bacteria, fungi, yeasts, insects, protozoa, cestodes and free-living nematodes. More recently they have been shownto have potent nematocidal activity against the free-living stages of intestinal parasitic nematodes of major importance in the animal health industry. Furthermore the bafilomycins have been suggested as possible therapeutic agents in the treatment of peptic ulceration, by virtue of their inhibition of cell vacuolisation induced by the bacterium Helicobacter pylori4~ 6\Themolecular structures of both the bafilomycins and the leucanicidins are characterised by the presence of a similar 1 6-membered macrolide nucleus to which various side chains are attached at the lactone terminus C15 (Fig. 1), leading to the generic term bafilolides for these antibiotics3*. The only bafilolide for which the complete stereochemistry has been rigorously secured is bafilomycin A1. X-ray crystallography of its 21-(2′, 2′, 2′-trichloroethylcarbonate) derivative established the absolute configuration depicted in structure 17), confirming that predicted from XHNMRdata and computer modeling in comparison with the known related antibiotic elaiophylin). Both crystalline and solution conformations of bafilomycin Axare stabilised by a hydrogen-bonding network involving C19-OH, C17-OH and C1= O, which fixes the configuration of the potentially epimerisable C19-hemiacetal hydroxyl group7’9~ 1 1].

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Bafilomycin A1

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