Tundrenone: An Atypical Secondary Metabolite from Bacteria with Highly Restricted Primary Metabolism.

Tundrenone: An Atypical Secondary Metabolite from Bacteria with Highly Restricted Primary Metabolism.
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DOI:
10.1021/jacs.7b12240
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发表时间:
2018-02-14
影响因子:
15
通讯作者:
Clardy J
Clardy J
中科院分区:
化学1区
文献类型:
--
作者:
Puri AW;Mevers E;Ramadhar TR;Petras D;Liu D;Piel J;Dorrestein PC;Greenberg EP;Lidstrom ME;Clardy J

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甲烷氧化菌是一种以甲烷为唯一碳源和能源的需氧菌,由于其对环境具有重要的去除大气中甲烷的能力而受到越来越多的研究。它们的基因组表明,它们也有一个强大的和不寻常的次级代谢。对Methylobacter tundripaludum基因组的生物信息学分析确定了几种有趣的代谢物的生物合成基因簇,本报告公开了这些代谢物之一tundrenone的结构和遗传特征。Tundrenone是一种高度氧化的代谢物,其包含修饰的双环分支酸衍生片段和修饰的脂质尾部,后者带有β,γ-不饱和α-羟基酮。Tundrenone与其生物合成基因簇有遗传联系,群体感应激活其生产。M. tundripaludum的基因组和tundrenone的发现支持了这样一种观点,即对甲烷氧化细菌的进一步研究将揭示新的天然分子支架和产生它们的生物合成途径。
Methane-oxidizing bacteria, aerobes that utilize methane as their sole carbon and energy source, are being increasingly studied for their environmentally significant ability to remove methane from the atmosphere. Their genomes indicate that they also have a robust and unusual secondary metabolism. Bioinformatic analysis of the Methylobacter tundripaludum genome identified biosynthetic gene clusters for several intriguing metabolites, and this report discloses the structural and genetic characterization of tundrenone, one of these metabolites. Tundrenone is a highly oxidized metabolite that incorporates both a modified bicyclic chorismate-derived fragment and a modified lipid tail bearing a β,γ-unsaturated α-hydroxy ketone. Tundrenone has been genetically linked to its biosynthetic gene cluster, and quorum sensing activates its production. M. tundripaludum’s genome and tundrenone’s discovery support the idea that additional studies of methane-oxidizing bacteria will reveal new naturally occurring molecular scaffolds and the biosynthetic pathways that produce them.
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