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Functional characterization of the halogenase SpmH and discovery of new deschloro tryptophan dimers

Abstract

The halogenase gene spmH was putatively involved in the biosynthesis of spiroindimicins/indimicins (SPMs/IDMs), a group of chlorinated tryptophan dimers (TDs) from deep-sea-derived Streptomyces sp. SCSIO 03032. Inactivation of spmH led to six deschloro-analogues of TDs, including four new compounds SPMs G (1) and H (2), and IDMs F (3) and G (4). Structures and absolute configurations of 1–4 were unambiguously determined by combination of extensive spectroscopic analysis, single-crystal X-ray diffraction and quantum chemical ECD calculations. Compounds 1 and 2 exhibited moderate cytotoxic activities against four cancer cell lines. Additionally, SpmH was biochemically characterized in vitro as an L-tryptophan 5-halogenase.

  • This article is part of the themed collection: Biosynthesis
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Publication details

The article was received on 07 Nov 2018, accepted on 06 Dec 2018 and first published on 06 Dec 2018


Article type: Communication
DOI: 10.1039/C8OB02775G
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Functional characterization of the halogenase SpmH and discovery of new deschloro tryptophan dimers

    Z. Liu, L. Ma, L. Zhang, W. Zhang, Y. Zhu, Y. Chen, W. Zhang and C. Zhang, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB02775G

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