Unusual (2R,6R)-bicyclo[3.1.1]heptane ring construction in fungal α-trans-bergamotene biosynthesis

Wen, Yanhua; Chen, Tian-Jiao; Jiang, Long-Yu; Li, Li; Guo, Mengbo; Yu, Peng; Chen, Jingjing; Pei, Fei; Yang, Jin-Ling; Wang, Ruishan; Gong, Ting; Zhu, Ping

doi:10.1016/j.isci.2022.104030

Cited by 6 publications

(4 citation statements)

References 72 publications

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“…The core gene of cluster 47 encodes a sesquiterpene cyclase (JGI protein ID: 291000) that shares a 74% identity to trichoacorenol ( 30 ) synthase NsTAS from Nectria sp. (Figure B) . This cluster has one additional conserved protein (JGI protein ID: 290978) that is predicted to be a heterokaryon incompatibility protein and is unlikely to be biosynthetic.…”

Section: Resultsmentioning

confidence: 99%

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Assessing the Biosynthetic Inventory of the Biocontrol Fungus Trichoderma afroharzianum T22

Wang

Zhong

et al. 2023

J. Agric. Food Chem.

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Natural products biosynthesized from biocontrol fungi in the rhizosphere can have both beneficial and deleterious effects on plants. Herein, we performed a comprehensive analysis of natural product biosynthetic gene clusters (BGCs) from the widely used biocontrol fungus Trichoderma afroharzianum T22 (ThT22). This fungus encodes at least 64 BGCs, yet only seven compounds and four BGCs were previously characterized or mined. We correlated 21 BGCs of ThT22 with known primary and secondary metabolites through homologous BGC comparison and characterized one unknown BGC involved in the biosynthesis of eujavanicol A using heterologous expression. In addition, we performed untargeted transcriptomics and metabolic analysis to demonstrate the activation of silent ThT22 BGCs via the “one strain many compound” (OSMAC) approach. Collectively, our analysis showcases the biosynthetic capacity of ThT22 and paves the way for fully exploring the roles of natural products of ThT22.

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Section: Resultsmentioning

confidence: 99%

“…(Figure 4B). 55 This cluster has one additional conserved protein (JGI protein ID: 290978) that is predicted to be a heterokaryon incompatibility protein and is unlikely to be biosynthetic.…”

Section: Cluster 47-trichoacorenolmentioning

confidence: 99%

Assessing the Biosynthetic Inventory of the Biocontrol Fungus Trichoderma afroharzianum T22

Wang

Zhong

et al. 2023

J. Agric. Food Chem.

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“…HLS206, BcBOS from B. cinerea B05.10 and LsBERS from Lachnellula suecica , have been reported to produce the enantiomers of 111 and 104 . 128 The catalytic mechanisms of these enzymes and how they precisely control the stereochemistry need further investigation. Recently, Tang et al used FmaTC as a query sequence and identified two UbiA-type cyclases, BC-TC and TV86-TC, from the fungus Botryotinia cinerea and T. virens , which produce compounds 103 and 111 , respectively.…”

Section: Terpenoid Cyclases In Fungal Terpenoid Biosynthesismentioning

confidence: 99%

Biosynthesis of fungal terpenoids

Luo,

Huang,

et al. 2024

Nat. Prod. Rep.

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“…However, there have been only a few synthetic methods toward BCH derivatives (Scheme C). The typical synthesis necessitated an intramolecular reaction of a suitably functionalized substrate, such as the biosynthetic cyclization of limonene-type molecules, photochemical cross [2π + 2π] cycloaddition of 1,6-dienes, or ring contraction of bicyclo[3.2.1]octanes . Very recently, elegant three component approaches using preformed [3.1.1] propellane as a reactant has been employed for efficient synthesis of bridge-substituted BCHs .…”

Section: Introductionmentioning

confidence: 99%

Selective [2σ + 2σ] Cycloaddition Enabled by Boronyl Radical Catalysis: Synthesis of Highly Substituted Bicyclo[3.1.1]heptanes

et al. 2023

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In contrast to the traditional and widely-used cycloaddition reactions involving at least a π bond component, a [2σ + 2σ] radical cycloaddition between bicyclo[1.1.0]butanes (BCBs) and cyclopropyl ketones has been developed to provide a modular, concise, and atom-economical synthetic route to substituted bicyclo[3.1.1]heptane (BCH) derivatives that are 3D bioisosteres of benzenes and core skeleton of a number of terpene natural products. The reaction was catalyzed by a combination of simple tetraalkoxydiboron(4) compound B 2 pin 2 and 3-pentyl isonicotinate. The broad substrate scope has been demonstrated by synthesizing a series of new highly functionalized BCHs with up to six substituents on the core with up to 99% isolated yield. Computational mechanistic investigations supported a pyridine-assisted boronyl radical catalytic cycle.

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Unusual (2R,6R)-bicyclo[3.1.1]heptane ring construction in fungal α-trans-bergamotene biosynthesis

Cited by 6 publications

References 72 publications

Assessing the Biosynthetic Inventory of the Biocontrol Fungus Trichoderma afroharzianum T22

Assessing the Biosynthetic Inventory of the Biocontrol Fungus Trichoderma afroharzianum T22

Biosynthesis of fungal terpenoids

Selective [2σ + 2σ] Cycloaddition Enabled by Boronyl Radical Catalysis: Synthesis of Highly Substituted Bicyclo[3.1.1]heptanes

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