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831 results on '"Oikawa, Hideaki"'

4. Subcellular compartmentalized localization of transmembrane proteins essential for production of fungal cyclic peptide cyclochlorotine.

Author

Katayama, Takuya, Jiang, Yulu, Ozaki, Taro, Oikawa, Hideaki, Minami, Atsushi, and Maruyama, Jun-ichi

Subjects
GREEN fluorescent protein, MEMBRANE proteins, CARRIER proteins, PEPTIDES, CHIMERIC proteins
Abstract

Fungal biosynthetic gene clusters often include genes encoding transmembrane proteins, which have been mostly thought to be transporters exporting the products. However, there is little knowledge about subcellular compartmentalization of transmembrane proteins essential for biosynthesis. Fungal mycotoxin cyclochlorotine is synthesized by non-ribosomal peptide synthetase, which is followed by modifications with three transmembrane UstYa-family proteins. Heterologous expression in Aspergillus oryzae revealed that total biosynthesis of cyclochlorotine requires additional two transporter proteins. Here, we investigated subcellular localizations of the five transmembrane proteins under heterologous expression in A. oryzae. Enhanced green fluorescent protein (EGFP) fusions to the transmembrane proteins, which were confirmed to normally function in cyclochlorotine production, were expressed together with organellar markers. All the transmembrane proteins exhibited localizations commonly in line of the trans -Golgi, endosomes, and vacuoles. This study suggests that subcellular compartmentalization of UstYa family proteins and transporters allows corporative functions of delivering intermediates and subsequent modifications, completing cyclochlorotine biosynthesis. [ABSTRACT FROM AUTHOR]

Published
2024
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7. Fungal-derived brevianamide assembly by a stereoselective semipinacolase

Author

Ye, Ying, Du, Lei, Zhang, Xingwang, Newmister, Sean A., McCauley, Morgan, Alegre-Requena, Juan V., Zhang, Wei, Mu, Shuai, Minami, Atsushi, Fraley, Amy E., Adrover-Castellano, Maria L., Carney, Nolan A., Shende, Vikram V., Qi, Feifei, Oikawa, Hideaki, Kato, Hikaru, Tsukamoto, Sachiko, Paton, Robert S., Williams, Robert M., Sherman, David H., and Li, Shengying

Published
2020
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15. A fungal sesquiterpene biosynthesis gene cluster critical for mutualist-pathogen transition in Colletotrichum tofieldiae

Author

55, 20714504, Hiruma, Kei, Aoki, Seishiro, Takino, Junya, Higa, Takeshi, Utami, Yuniar Devi, Shiina, Akito, Okamoto, Masanori, Nakamura, Masami, Kawamura, Nanami, Ohmori, Yoshihiro, Sugita, Ryohei, Tanoi, Keitaro, Sato, Toyozo, Oikawa, Hideaki, Minami, Atsushi, Iwasaki, Wataru, 154, 50587764, Saijo, Yusuke, 55, 20714504, Hiruma, Kei, Aoki, Seishiro, Takino, Junya, Higa, Takeshi, Utami, Yuniar Devi, Shiina, Akito, Okamoto, Masanori, Nakamura, Masami, Kawamura, Nanami, Ohmori, Yoshihiro, Sugita, Ryohei, Tanoi, Keitaro, Sato, Toyozo, Oikawa, Hideaki, Minami, Atsushi, Iwasaki, Wataru, 154, 50587764, and Saijo, Yusuke

Abstract

Plant-associated fungi show diverse lifestyles from pathogenic to mutualistic to the host; however, the principles and mechanisms through which they shift the lifestyles require elucidation. The root fungus Colletotrichum tofieldiae (Ct) promotes Arabidopsis thaliana growth under phosphate limiting conditions. Here we describe a Ct strain, designated Ct3, that severely inhibits plant growth. Ct3 pathogenesis occurs through activation of host abscisic acid pathways via a fungal secondary metabolism gene cluster related to the biosynthesis of sesquiterpene metabolites, including botrydial. Cluster activation during root infection suppresses host nutrient uptake-related genes and changes mineral contents, suggesting a role in manipulating host nutrition state. Conversely, disruption or environmental suppression of the cluster renders Ct3 beneficial for plant growth, in a manner dependent on host phosphate starvation response regulators. Our findings indicate that a fungal metabolism cluster provides a means by which infectious fungi modulate lifestyles along the parasitic–mutualistic continuum in fluctuating environments., journal article

Published
2023

23. Biosynthesis of Cyclochlorotine : Identification of the Genes Involved in Oxidative Transformations and Intramolecular O,N-Transacylation

Author

Jiang, Yulu, Ozaki, Taro, Liu, Chengwei, Igarashi, Yuya, Ye, Ying, Tang, Shoubin, Ye, Tao, Maruyama, Jun-Ichi, Minami, Atsushi, and Oikawa, Hideaki

Abstract

Mycotoxin cyclochlorotine (1) and structurally related astins are cyclic pentapeptides containing unique nonproteinogenic amino acids, such as beta-phenylalanine, L-allo-threonine, and 3,4-dichloroproline. Herein, we report the biosynthetic pathway for 1, which involves intriguing tailoring processes mediated by DUF3328 proteins, including stereo- and regiospecific chlorination and hydroxylation and intramolecular O,N-transacylation. Our findings demonstrate that DUF3328 proteins, which are known to be involved in oxidative cyclization of fungal ribosomal peptides, have much higher functional diversity than previously expected.

Published
2021

30. Zn(OTf)2-mediated annulations of N-propargylated tetrahydrocarbolines: divergent synthesis of four distinct alkaloidal scaffolds† †Electronic supplementary information (ESI) available. CCDC 1905889, 1905890 and 1905916. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc01507h

Author

Yorimoto, Sadaiwa, Tsubouchi, Akira, Mizoguchi, Haruki, Oikawa, Hideaki, Tsunekawa, Yoshiaki, Ichino, Tomoya, Maeda, Satoshi, and Oguri, Hiroki

Subjects
Chemistry
Abstract

Experimental and computational studies gained insights into Zn(OTf)2-mediated annulations and allowed programmable synthesis of four distinct alkaloidal scaffolds., Intramolecular hydroarylations of N-propargylated tetrahydrocarbolines were efficiently mediated using a unique combination of Zn(OTf)2 with t-BuOH under neutral conditions. Use of the artificial force induced reaction method in the global reaction route mapping strategy provided insights into the Zn(OTf)2-mediated hydroarylations and the associated intriguing solvent effects of t-BuOH facilitating a protodezincation process without a Brønsted acid activator. We systematically implemented three distinct hydroarylations as well as an unanticipated α-alkenylation of a carbonyl group to obtain the four alkaloidal scaffolds 2–4, and 18. Zn(OTf)2-mediated annulation of 1c proceeded through kinetic formation of the spiroindole 3c followed by an alkenyl shift and concomitant retro-Mannich-type fragmentation to furnish azepino[4,5-b]indole 2 framework. Substituents on substrate 1 in the vicinity of the reaction sites substantially affected the mode of the divergent annulations. Judicious choices of the substituents, solvent and reaction conditions enabled programmable divergent synthesis of the four distinct skeletons.

Published
2019

35. Enzymatic catalysis of anti-Baldwin ring closure in polyether biosynthesis

Author

Hotta, Kinya, Chen, Xi, Paton, Robert S., Minami, Atsushi, Li, Hao, Swaminathan, Kunchithapadam, Mathews, Irimpan I., Watanabe, Kenji, Oikawa, Hideaki, Houk, Kendall N., and Kim, Chu-Young

Subjects
Chemical properties, Composition, Research, Microbial enzymes -- Research -- Chemical properties, Biosynthesis -- Research -- By-products, Crystal structure -- Research, Polyethers -- Research -- Chemical properties -- Composition, Crystals -- Structure, Glycol ethers -- Research -- Chemical properties -- Composition
Abstract

Epoxide-opening cascades, including those using the disfavoured anti-Baldwin cyclization (Fig. 1a), have emerged as an important synthetic strategy in the field of organic chemistry (10). Whereas little is known about [...], Polycyclic polyether natural products have fascinated chemists and biologists alike owing to their useful biological activity, highly complex structure and intriguing biosynthetic mechanisms. Following the original proposal for the polyepoxide origin of lasalocid and isolasalocid (1) and the experimental determination of the origins of the oxygen and carbon atoms of both lasalocid and monensin, a unified stereochemical model for the biosynthesis of polyether ionophore antibiotics was proposed (2). The model was based on a cascade of nucleophilic ring closures of postulated polyepoxide substrates generated by stereospecific oxidation of all-trans polyene polyketide intermediates (2). Shortly thereafter, a related model was proposed for the biogenesis of marine ladder toxins, involving a series of nominally disfavoured anti-Baldwin, endo-tet epoxide-ring-opening reactions (3-5). Recently, we identified Lsd19 from the Streptomyces lasaliensis gene cluster as the epoxide hydrolase responsible for the epoxide-opening cyclization of bisepoxyprelasalocid A (6) to form lasalocid A (7,8). Here we report the X-ray crystal structure of Lsd19 in complex with its substrate and product analogue (9) to provide the first atomic structure--to our knowledge--of a natural enzyme capable of catalysing the dis-favoured epoxide-opening cyclic ether formation. On the basis of our structural and computational studies, we propose a general mechanism for the enzymatic catalysis of polyether natural product biosynthesis.

Published
2012

37. Genome-Based Discovery of Enantiomeric Pentacyclic Sesterterpenes Catalyzed by Fungal Bifunctional Terpene Synthases

Author

Jiang, Lan, primary, Zhang, Xue, additional, Sato, Yuya, additional, Zhu, Guoliang, additional, Minami, Atsushi, additional, Zhang, Weiyan, additional, Ozaki, Taro, additional, Zhu, Bin, additional, Wang, Zhixin, additional, Wang, Xinye, additional, Lv, Kangjie, additional, Zhang, Jingyu, additional, Wang, Yongheng, additional, Gao, Shushan, additional, Liu, Chengwei, additional, Hsiang, Tom, additional, Zhang, Lixin, additional, Oikawa, Hideaki, additional, and Liu, Xueting, additional

Published
2021
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38. Biosynthetic Studies of Phomopsins Unveil Posttranslational Installation of Dehydroamino Acids by UstYa Family Proteins

Author

Sogahata, Kaho, Ozaki, Taro, Igarashi, Yuya, Naganuma, Yuka, Liu, Chengwei, Minami, Atsushi, 1000000185175, Oikawa, Hideaki, Sogahata, Kaho, Ozaki, Taro, Igarashi, Yuya, Naganuma, Yuka, Liu, Chengwei, Minami, Atsushi, 1000000185175, and Oikawa, Hideaki

Abstract

UstYa family proteins (DUF3328) are widely and specifically distributed in fungi. They are known to be involved in the biosynthesis of ribosomally synthesized and posttranslationally modified peptides (RiPPs) and nonribosomal peptides, and possibly catalyze various reactions, including oxidative cyclization and chlorination. In this study, we focused on phomopsin A, a fungal RiPP consisting of unique nonproteinogenic amino acids. Gene knockout experiments demonstrated that three UstYa homologues, phomYc, phomYd, and phomYe, are essential for the desaturation of amino acid moieties, showing unprecedented function among UstYa family proteins. Sequence similarity network analysis indicated that their amino acid sequences are highly diverged and that most remain uncharacterized, paving the way for genome mining of fungal metabolites with unique modifications.

Published
2021

44. Proposed mechanism for the reaction catalyzed by a diterpene cyclase, aphidicolan-16beta-ol synthase: Experimental results on biomimetic cyclization and examination of the cyclization pathway by ab inito calculations

Author

Oikawa, Hideaki, Nakamura, Kensuke, Toshima, Hiroaki, Toyomasu, Tomonobu, and Sassa, Takeshi

Subjects
Transition state (Chemistry) -- Research, Diterpenes -- Structure, Diterpenes -- Chemical properties, Enzymatic analysis, Chemistry
Abstract

A detailed reaction pathway for the Lewis acid-catalyzed cyclizations and rearrangements is proposed. Ab inito calculations of the acid-catalyzed reaction intermediates and the transition states indicate that the overall reaction catalyzed by ACS is an exothermic process though the reaction proceeds via an energetically disfavored secondary cation-like transition state.

Published
2002

47. Biosynthesis of Indole Diterpene Lolitrems: Radical‐Induced Cyclization of an Epoxyalcohol Affording a Characteristic Lolitremane Skeleton

Author

Jiang, Yulu, primary, Ozaki, Taro, additional, Harada, Mei, additional, Miyasaka, Tadachika, additional, Sato, Hajime, additional, Miyamoto, Kazunori, additional, Kanazawa, Junichiro, additional, Liu, Chengwei, additional, Maruyama, Jun‐ichi, additional, Adachi, Masaatsu, additional, Nakazaki, Atsuo, additional, Nishikawa, Toshio, additional, Uchiyama, Masanobu, additional, Minami, Atsushi, additional, and Oikawa, Hideaki, additional

Published
2020
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48. Rapid and Systematic Exploration of Chemical Space Relevant to Artemisinins: Anti-malarial Activities of Skeletally Diversified Tetracyclic Peroxides and 6-Aza-artemisinins

Author

Bonepally, Karunakar Reddy, primary, Takahashi, Norihito, additional, Matsuoka, Naoya, additional, Koi, Hikari, additional, Mizoguchi, Haruki, additional, Hiruma, Takahisa, additional, Ochiai, Kyohei, additional, Suzuki, Shun, additional, Yamagishi, Yutaka, additional, Oikawa, Hideaki, additional, Ishiyama, Aki, additional, Hokari, Rei, additional, Iwatsuki, Masato, additional, Otoguro, Kazuhiko, additional, O̅mura, Satoshi, additional, Kato, Nobutaka, additional, and Oguri, Hiroki, additional

Published
2020
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