Zhiyang Quan

Biosynthesis and enzymology of azaindane natural products

Zhiyang Quan, Takayoshi Awakawa

As a representative example of biosynthetic genome mining aimed at identifying biosynthetic gene clusters whose target is unknown core enzymes for known natural products, we review the biosynthesis of altemicidin (1), SB-203207 (2), and SB-203208 (3). Self-resistance gene-guided genome mining led to …

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Search for Inhibitors against Inflammatory Responses of Microglia in a Meroterpenoid Library Constructed by Synthetic–Biological Manipulation of Biosynthetic Pathways

Kanako Takahashi, Zhiyang Quan, Yukari Shigemoto‐Mogami, Beibei Zhang et autres

High Resolution Image Download MS PowerPoint Slide Microglia are the resident immune cells of the central nervous system. Activation-induced proinflammatory responses of microglia are associated with various neurodegenerative diseases, and therefore, inhibitors against microglial inflammatory responses are promising candidates for the treatment …

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Structural and Mechanistic Basis for Orthoester Formation by αKG-Free Endoperoxide Isomerase in Novofumigatonin Biosynthesis

Y. Yang, Xuan Kai Zhang, Takahiro Mori, Zhiyang Quan et autres

Orthoester-containing natural products possess unique oxygen-rich architectures; however, the enzymatic mechanism responsible for constructing these functional groups has remained unclear. In this study, we report the structure–function analysis of NvfE, a nonheme iron enzyme from Aspergillus novofumigatus, which catalyzes the Fe(II)-dependent isomerization …

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Structural Basis for 3-Amino-3-carboxypropyl Transfer in Nocardicin Biosynthesis

Yaojie Gao, Masayuki Karasawa, Zhiyang Quan, Takahiro Mori et autres

S -Adenosyl- l -methionine (SAM) is well-known as a methyl donor for methyltransferases but also functions as a 3-amino-3-carboxypropyl (3-ACP) donor for 3-ACP transferases. NAT is a 3-ACP transferase which accepts β-lactam antibiotic nocardicin G ( 1 ) and SAM to produce …

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Discovery of (±)‐Penindolenes Reveals an Unusual Indole Ring Cleavage Pathway Catalyzed by P450 Monooxygenase

Ling‐Hong Meng, Takayoshi Awakawa, Xiaoming Li, Zhiyang Quan et autres

Abstract (±)‐Penindolenes A−D (1–4), the first representatives of indole terpenoids featuring a γ‐lactam skeleton, were isolated from the mangrove‐derived endophytic fungus Penicillium brocae MA‐231. Our bioactivity tests revealed their potent antimicrobial and acetylcholinesterase inhibitory activities. The biosynthetic reactions by the five enzymes …

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Discovery of (±)‐Penindolenes Reveals an Unusual Indole Ring Cleavage Pathway Catalyzed by P450 Monooxygenase

Ling‐Hong Meng, Takayoshi Awakawa, Xiao‐Ming Li, Zhiyang Quan et autres

(±)-Penindolenes A-D (1-4), the first representatives of indole terpenoids featuring a γ-lactam skeleton, were isolated from the mangrove-derived endophytic fungus Penicillium brocae MA-231. Our bioactivity tests revealed their potent antimicrobial and acetylcholinesterase inhibitory activities. The biosynthetic reactions by the five enzymes PbaABCDE …

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Recent developments in the engineered biosynthesis of fungal meroterpenoids

Zhiyang Quan, Takayoshi Awakawa

Meroterpenoids are hybrid compounds that are partially derived from terpenoids. This group of natural products displays large structural diversity, and many members exhibit beneficial biological activities. This mini-review highlights recent advances in the engineered biosynthesis of meroterpenoid compounds with C15 and C20 …

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CCDC 2289117: Experimental Crystal Structure Determination

Jeroen S. Dickschat, Zhiyang Quan, Gregor Schnakenburg

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, …

CCDC 2289118: Experimental Crystal Structure Determination

Jeroen S. Dickschat, Zhiyang Quan, Gregor Schnakenburg

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, …

A Case of Convergent Evolution: The Bacterial Sesquiterpene Synthase for 1‐epi‐Cubenol from Nonomuraea coxensis

Jeroen S. Dickschat, Zhiyang Quan, Gregor Schnakenburg

A terpene synthase from Nonomuraea coxensis was identified as (+)-1-epi-cubenol synthase. The enzyme is phylogenetically unrelated to the known enzyme of the same function that is widespread in streptomycetes. Isotopic labelling experiments were performed to unambiguously assign the NMR data and to …

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Mechanism of the Bifunctional Multiple Product Sesterterpene Synthase AcAS from Aspergillus calidoustus

Zhiyang Quan, Anwei Hou, Bernd Goldfuß, Jeroen S. Dickschat

The multiproduct chimeric sesterterpene synthase AcAS from Aspergillus calidoustus yielded spirocyclic calidoustene, which exhibits a novel skeleton, besides five known sesterterpenes. The complex cyclisation mechanism to all six compounds was investigated by isotopic labelling experiments in combination with DFT calculations. Chemically synthesised …

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Mechanismus der bifunktionellen Multiprodukt‐Sesterterpensynthase AcAS aus Aspergillus calidoustus

Zhiyang Quan, Anwei Hou, Bernd Goldfuß, Jeroen S. Dickschat

Abstract Die chimäre Multiprodukt‐Sesterterpensynthase AcAS aus Aspergillus calidoustus lieferte neben fünf bekannten Sesterterpenen das spirocyclische Calidousten, welches ein neues Gerüst aufweist. Der komplexe Cyclisierungsmechanismus zu allen sechs Verbindungen wurde durch Isotopenmarkierungsexperimente in Kombination mit DFT‐Rechnungen untersucht. Chemisch synthetisiertes 8‐Hydroxyfarnesyldiphosphat wurde mit Isopentenyldiphosphat …

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