Biosynthesis of sydonol reveals a new bisabolene cyclase and an unusual P450 aromatase

In this work, the biosynthetic gene cluster and assembly line of sydonol were discovered and identified. As a result, and importantly, two unusual chemical conversions catalyzed by a new bisabolene cyclase and an unusual P450 aromatase were revealed: (1) cyclization of FPP to form 2, which involves a unique 1,5-proton transfer and a 1,7-hydride shift; and (2) aromatization of a bisabolene skeleton in the synthesis of 7.

• Publication year

  2025

• Venue

  RSC Chemical Biology

• Publication date

  2025-09-04

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/d5cb00213cPMID 40958939PMCID 12434612
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Targeting the cysteine biosynthesis pathway in microorganisms: Mechanism, structure, and drug discovery.

  2024cited by this paper
• Sulfoxide-Containing Bisabolane Sesquiterpenoids with Antimicrobial and Nematicidal Activities from the Marine-Derived Fungus Aspergillus sydowii LW09

  2023cited by this paper
• Two Pairs of New Bisabolane‐Type Sesquiterpenoids from Aspergillus sydowii

  2023cited by this paper
• Bisabolane-Type Sesquiterpenoids with a Tetrahydrofuran or Tetrahydropyran Ring from Vernonia solanifolia.

  2023cited by this paper
• Structural Insights into Three Sesquiterpene Synthases for the Biosynthesis of Tricyclic Sesquiterpenes and Chemical Space Expansion by Structure-Based Mutagenesis.

  2023cited by this paper
• New Bisabolane-Type Sesquiterpenoids from Curcuma longa and Their Anti-Atherosclerotic Activity

  2023cited by this paper
• Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

  2022cited by this paper
• Rerouting and Improving Dauc‐8‐en‐11‐ol Synthase from Streptomyces venezuelae to a High Yielding Biocatalyst

  2021cited by this paper
• Bisabolane-type sesquiterpenoids: Structural diversity and biological activity.

  2021cited by this paper
• Sesquiterpene synthases for bungoene, pentalenene and epi-isozizaene from Streptomyces bungoensis.

  2020cited by this paper
• Antimicrobial bisabolane-type sesquiterpenoids from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330

  2019cited by this paper
• Comment on "Substrate Folding Modes in Trichodiene Synthase: A Determinant of Chemo- and Stereoselectivity".

  2018cited by this paper
• Chemical Control in the Battle against Fidelity in Promiscuous Natural Product Biosynthesis: The Case of Trichodiene Synthase.

  2017cited by this paper
• Discovery of Unclustered Fungal Indole Diterpene Biosynthetic Pathways through Combinatorial Pathway Reassembly in Engineered Yeast.

  2015cited by this paper
• Branching out from the bisabolyl cation. Unifying mechanistic pathways to barbatene, bazzanene, chamigrene, chamipinene, cumacrene, cuprenene, dunniene, isobazzanene, iso-γ-bisabolene, isochamigrene, laurene, microbiotene, sesquithujene, sesquisabinene, thujopsene, trichodiene, and widdradiene sesqu

  2014cited by this paper
• Diverse functional evolution of serine decarboxylases: identification of two novel acetaldehyde synthases that uses hydrophobic amino acids as substrates

  2014cited by this paper
• The fumagillin biosynthetic gene cluster in Aspergillus fumigatus encodes a cryptic terpene cyclase involved in the formation of β-trans-bergamotene.

  2013cited by this paper
• Biosynthesis of Sesquiterpenes by the Fungus Fusarium verticillioides

  2011cited by this paper
• Sesquiterpene Synthases Cop4 and Cop6 from Coprinus cinereus: Catalytic Promiscuity and Cyclization of Farnesyl Pyrophosphate Geometric Isomers

  2010cited by this paper
• Consequences of conformational preorganization in sesquiterpene biosynthesis: theoretical studies on the formation of the bisabolene, curcumene, acoradiene, zizaene, cedrene, duprezianene, and sesquithuriferol sesquiterpenes.

  2009cited by this paper
• Expression of a synthetic Artemesia annua amorphadiene synthase in Aspergillus nidulans yields altered product distribution

  2008cited by this paper
• Multiple fungal enzymes possess cysteine synthase activity in vitro.

  2007cited by this paper
• Two sesquiterpene synthases are responsible for the complex mixture of sesquiterpenes emitted from Arabidopsis flowers.

  2005cited by this paper

• Nitrogen-Containing Sesquiterpenoids from the Sponge Stellitethya ingens as TRPA1 Antagonists.

  2025cites this paper