Issue 5, 2019

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). 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

Supplementary files

Article information

Article type
Communication
Submitted
07 Nov. 2018
Accepted
06 Dec. 2018
First published
06 Dec. 2018

Org. Biomol. Chem., 2019,17, 1053-1057

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, 17, 1053 DOI: 10.1039/C8OB02775G

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