鉴定并阐明蓝藻门织线藻目中的 welwitindolinone 生物碱生物合成基因簇。
Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii.
出版信息
Chembiochem. 2014 Mar 21;15(5):665-9. doi: 10.1002/cbic.201300794.
Abstract
The identification of a 36 kb welwitindolinone (wel) biosynthetic gene cluster in Hapalosiphon welwitschii UTEX B1830 is reported. Characterization of the enzymes responsible for assembling the early biosynthetic intermediates geranyl pyrophosphate and 3-((Z)-2′-isocyanoethenyl)indole as well as a dedicated N-methyltransferase in the maturation of N-methylwelwitindolinone C isothiocyanate solidified the link between the wel pathway and welwitindolinone biosynthesis. Comparative analysis of the ambiguine and welwitindolinone biosynthetic pathways in two different organisms provided insights into the origins of diverse structures within hapalindole-type molecules.
摘要
报道了在 Hapalosiphon welwitschii UTEX B1830 中鉴定出一个 36kb 的 welwitindolinone（wel）生物合成基因簇。负责组装早期生物合成中间体香叶基焦磷酸和 3-((Z)-2′-异氰基乙烯基)吲哚以及在 N-甲基welwitindolinone C 异硫氰酸甲酯成熟过程中专用 N-甲基转移酶的酶的表征，巩固了 wel 途径与 welwitindolinone 生物合成之间的联系。在两个不同生物体中对 ambiguine 和 welwitindolinone 生物合成途径的比较分析，深入了解了 hapalindole 型分子中不同结构的起源。
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2
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3
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4
A tRNA-dependent two-enzyme pathway for the generation of singly and doubly methylated ditryptophan 2,5-diketopiperazines.tRNA 依赖性双酶途径用于生成单甲基和双甲基二色氨酸 2,5-二酮哌嗪。
Biochemistry. 2013 Jun 18;52(24):4274-83. doi: 10.1021/bi4004827. Epub 2013 Jun 7.
5
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6
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7
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