Naphthol radical couplings determine structural features and enantiomeric excess of dalesconols in Daldinia eschscholzii

Wei Fang, Shen Ji, Nan Jiang, Wei Wang, Guo Yan Zhao, Su Zhang, Hui Ming Ge, Qiang Xu, Ai Hua Zhang, Ying Lao Zhang, Yong Chun Song, Jie Zhang and Ren Xiang Tan ()
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Wei Fang: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Shen Ji: Shanghai Institute of Food & Drug Controls
Nan Jiang: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Wei Wang: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Guo Yan Zhao: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Su Zhang: Shanghai Institute of Food & Drug Controls
Hui Ming Ge: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Qiang Xu: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Ai Hua Zhang: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Ying Lao Zhang: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Yong Chun Song: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Jie Zhang: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University
Ren Xiang Tan: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University

Nature Communications, 2012, vol. 3, issue 1, 1-9

Abstract: Abstract Understanding how simple molecules are pieced together in organisms may aid biotechnological manipulation and synthetic approaches to complex natural products. The mantis-associated fungus Daldinia eschscholzii IFB-TL01 produces the unusually structured immunosuppressants (±)-dalesconols A and B, along with their congener (±)-dalesconol C, with the (−)-enantiomers in excess. Here we report that these structural and stereochemical peculiarities of dalesconols A–C are a result of promiscuous and atropselective couplings of radicals derived from 1,3,6,8-tetrahydroxynaphthalene, 1,3,8-trihydroxynaphthalene and 1,8-dihydroxynaphthalene. The observed (−)-enantiomeric excess is found to depend on the dominance of particular conformers of naphthol dimer intermediates, which are ligands of laccase.

Date: 2012
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DOI: 10.1038/ncomms2031

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