Scholarlink

<p>Butenolides are important features of many bioactive compounds. Current petrochemical-based methods for asymmetric butenolide synthesis are unsustainable. Biocatalysis could enable cheaper, greener, and more sustainable alternatives. However, known butenolide biosynthetic pathways are complex and challenging to harness. Here we show that avenolide, a 4-alkylbutenolide that regulates avermectin production in <i>Streptomyces avermitilis</i>, is assembled from a fatty acyl thioester by a multifunctional flavoenzyme and an iterative cytochrome P450. The flavoenzyme catalyzes homochiral 4-alkylbutenolide formation via successive desaturation, hydroxylation, and lactonization reactions, using dioxygen as the sole stoichiometric reagent. This lays the foundation for development of sustainable biocatalytic asymmetric butenolide synthesis.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Trifunctional flavoenzyme-catalyzed asymmetric 4-alkyl-butenolide assembly in avenolide biosynthesis

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年2月7日

查看全文
  • Wenrui Li,
  • Jinlian Zhao,
  • Weibo Zeng,
  • Ruifei Zhang,
  • Lei Yan,
  • Yuting Fan,
  • Jiaxin Liu,
  • Wenzhao Wang,
  • Gregory L. Challis,
  • Shanshan Zhou

摘要

Butenolides are important features of many bioactive compounds. Current petrochemical-based methods for asymmetric butenolide synthesis are unsustainable. Biocatalysis could enable cheaper, greener, and more sustainable alternatives. However, known butenolide biosynthetic pathways are complex and challenging to harness. Here we show that avenolide, a 4-alkylbutenolide that regulates avermectin production in Streptomyces avermitilis, is assembled from a fatty acyl thioester by a multifunctional flavoenzyme and an iterative cytochrome P450. The flavoenzyme catalyzes homochiral 4-alkylbutenolide formation via successive desaturation, hydroxylation, and lactonization reactions, using dioxygen as the sole stoichiometric reagent. This lays the foundation for development of sustainable biocatalytic asymmetric butenolide synthesis.