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Issue 47, 2018
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StnK2 catalysing a Pictet–Spengler reaction involved in the biosynthesis of the antitumor reagent streptonigrin

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Abstract

Streptonigrin (STN, 1) is a highly functionalized aminoquinone alkaloid antibiotic with broad and potent antitumor activity. Previous isotope-labelling and genetic studies suggested that a β-carboline alkaloid should be a key intermediate of STN biosynthesis and formed via a Pictet–Spengler (PS) reaction. Herein, StnK2 was biochemically characterized to be a Pictet–Spenglerase (PSase) catalysing the formation of a tetrahydro-β-carboline (TH-βC) scaffold from (2S,3S)-β-methyl tryptophan and D-erythrose-4-phosphate. StnK2 can tolerate the alteration of tryptophan but only accept D-erythrose-4-phosphate as the aldehyde substrate, and StnK2 was identified to be R-specific for the newly formed chiral center. This work increases the diversities of Pictet–Spenglerase in nature and set a stage for the generation of streptonigrin derivatives by precursor-directed pathway engineering based on the flexible substrate selectivity of StnK2.

Graphical abstract: StnK2 catalysing a Pictet–Spengler reaction involved in the biosynthesis of the antitumor reagent streptonigrin

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Publication details

The article was received on 31 Oct 2018, accepted on 19 Nov 2018 and first published on 28 Nov 2018


Article type: Communication
DOI: 10.1039/C8OB02710B
Citation: Org. Biomol. Chem., 2018,16, 9124-9128
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    StnK2 catalysing a Pictet–Spengler reaction involved in the biosynthesis of the antitumor reagent streptonigrin

    X. Wang, D. Kong, T. Huang, Z. Deng and S. Lin, Org. Biomol. Chem., 2018, 16, 9124
    DOI: 10.1039/C8OB02710B

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