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The Synthesis and Biological Evaluation of Desepoxyisotedanolide and a Comparison with Desepoxytedanolide
Author(s) -
Naini Arun,
Muthukumar Yazh,
Raja Aruna,
Franke Raimo,
Harrier Ian,
Smith Amos B.,
Lee Dongjoo,
Taylor Richard E.,
Sasse Florenz,
Kalesse Markus
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501526
Subject(s) - transesterification , biological activity , alcohol , computational biology , biology , primary (astronomy) , chemistry , combinatorial chemistry , organic chemistry , biochemistry , catalysis , in vitro , physics , astronomy
The tedanolides are biologically active polyketides that exhibit a macrolactone constructed from a primary alcohol. Since polyketidal transformations only generate secondary alcohols, it has been hypothesized by Taylor that this unique lactone could arise from a postketidal transesterification. In order to probe this hypothesis and to investigate the biological profile of the putative precursor of all members of the tedanolide family, we embarked on the synthesis of desepoxyisotedanolide and its biological evaluation in comparison to desepoxytedanolide. The biological experiments unraveled a second target for desepoxytedanolide and provided evidence that the proposed transesterification indeed provides a survival advantage for the producing microorganism.