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

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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). The structures and absolute configurations of 1–4 were unambiguously determined by the 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.

Graphical abstract: Functional characterization of the halogenase SpmH and discovery of new deschloro-tryptophan dimers

  • 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., 2019, Advance Article
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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., 2019, Advance Article , DOI: 10.1039/C8OB02775G

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