Biosynthesis of Epipyrone A Reveals a Highly Specific Membrane-Bound Fungal C-Glycosyltransferase for Pyrone Galactosylation,Organic Letters

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Biosynthesis of Epipyrone A Reveals a Highly Specific Membrane-Bound Fungal C-Glycosyltransferase for Pyrone Galactosylation
Organic Letters ( IF 4.9 ) Pub Date : 2024-02-06 , DOI: 10.1021/acs.orglett.3c04259
Aili Fan ₁ , Boyuan Zhong _{1,

2} , Dong Liu _{1,

3} , Yubo Lu ₁ , Mengyue Wu ₁ , Hongwei Jin ₁ , Xiao-Meng Shi ₁ , Jinwei Ren ₄ , Bo Zhang ₂ , Xiao-Dong Su ₂ , Ming Ma ₁ , Shu-Ming Li ₅ , Wenhan Lin _{1,

3}

Affiliation

Epipyrone A is a unique C-galactosylated 4-hydroxy-2-pyrone derivative with an antifungal potential from the fungus Epicoccum nigrum. We elucidated its biosynthesis via heterologous expression and characterized an unprecedented membrane-bound pyrone C-glycosyltransferase biochemically. Molecular docking and mutagenesis experiments suggested a possible mechanism for the heterocyclic C-glycosylation and the importance of a transmembrane helix for its catalysis. These results expand the repertoire of C-glycosyltransferases and provide new insights into the formation of C-glycosides in fungi.

中文翻译：

Epipyrone A 的生物合成揭示了一种用于吡喃酮半乳糖基化的高度特异性膜结合真菌 C-糖基转移酶

Epipyrone A 是一种独特的C-半乳糖基化 4-羟基-2-吡喃酮衍生物，具有来自真菌Epicocum nigrum的抗真菌潜力。我们通过异源表达阐明了其生物合成，并通过生物化学方法表征了前所未有的膜结合吡喃酮C-糖基转移酶。分子对接和诱变实验表明杂环C-糖基化的可能机制以及跨膜螺旋对其催化的重要性。这些结果扩大了C-糖基转移酶的范围，并为真菌中C-糖苷的形成提供了新的见解。

更新日期：2024-02-06

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