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Communication | Regular issue | Vol 31, No. 11, 1990, pp.1907-1913
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5555
Secondary Metabolites by Chemical Screening. 11. Influence of the C-1 and C-29 Moieties in Nigericin on Complexation Behaviour and Biological Activity

Susanne Grabley, Peter Hammann,* Robert Klein, and Michael Magerstädt

*Hoechst AG, Postfach 80 03 20, D-65926 Frankfurt a. Main, Germany

Abstract

A reversible blocking of the C-29 hemiacetal in nigericin (1) was performed with LiBr in methanol to the acetal (6). Conversion of the carboxylic acid to the C-1 alcohol (7) and the ketone (9) and the subsequent deprotection yielded 8 and 10, respectively leaving F-rings intact. Complexation- and molecular medelling-studies with the nigericin alcohols (7) and (8) demonstrated the importance of noncyclic conformations.