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

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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
    School of Pharmacy, Nanjing Medical 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)

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.

Suggested Citation

  • 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 & Ren Xiang Tan, 2012. "Naphthol radical couplings determine structural features and enantiomeric excess of dalesconols in Daldinia eschscholzii," Nature Communications, Nature, vol. 3(1), pages 1-9, January.
    • Handle: RePEc:nat:natcom:v:3:y:2012:i:1:d:10.1038_ncomms2031
    DOI: 10.1038/ncomms2031
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