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

文献情報

出版日 2018-12-06

DOI 10.1039/C8OB02775G

インパクトファクター 3.876

著者

Zhiwen Liu, Liang Ma, Liping Zhang, Wenjun Zhang, Yiguang Zhu, Yuchan Chen, Weimin Zhang, Changsheng Zhang

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要旨

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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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

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