研究者詳細 - 岡内　辰夫

論文 - 岡内　辰夫

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A Convenient Method for Synthesizing 1-Alkyl-2-Acyl-sn-Glycero-3-Phosphoethanolamines 査読有り国際誌

Okauchi T., Tsubaki K., Higuma Y., Shimooka H., Kitamura M.

Synthesis (Germany) 56 ( 11 ) 1787 - 1792 2024年02月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

A convenient method for synthesizing 1-Alkyl-2-Acyl-sn-glycero-3-phosphoethanolamines starting from an optical active alcohol is described. In this method, the phosphate group was introduced through the transesterification that we developed, and a protected 1-Alkyl-2-lyso-GPE was employed as an intermediate. This compound is stable and serves as a common intermidiate for the synthesis of various 1-Alkyl-2-Acyl-GPEs with different acyl groups.

DOI： 10.1055/a-2257-0684

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KIT-13, a novel plasmalogen derivative, attenuates neuroinflammation and amplifies cognition 査読有り

Hossain M.S., Mawatari S., Honsho M., Okauchi T., Fujino T.

Frontiers in Cell and Developmental Biology 12 2024年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

Plasmalogens (Pls) are specialized phospholipids integral to brain health, whose decline due to aging and stress contributes to cognitive impairment and neuroinflammation. This study explores the potential of a novel Pls derivative, KIT-13 (1-O-octadecyl-2-arachidonoyl-sn-glycerol-3-phosphoethanolamine), in mitigating neuroinflammation and enhancing cognition. When administered to mice, KIT-13 exhibited potent memory enhancement attributed to upregulated brain-derived neurotrophic factor (BDNF), a key player in cognitive processes. In vitro experiments with neuronal cells revealed KIT-13’s ability to induce robust cellular signaling, surpassing natural plasmalogens. KIT-13 also promoted neurogenesis and inhibited apoptosis of neuronal-like cells, highlighting its potential in fostering neuronal growth and plasticity. Additionally, KIT-13 treatments reduced pro-inflammatory cytokine expression and attenuated glial activation in the brain. KIT-13’s superior efficacy over natural Pls positions it as a promising therapeutic candidate for neurodegenerative conditions such as Alzheimer’s disease, characterized by cognitive decline and neuroinflammation. This study presents KIT-13 as an innovative approach for addressing cognitive impairment and neuroinflammatory pathologies.

DOI： 10.3389/fcell.2024.1443536

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Diazo-Transfer Reaction of Nonactivated Ketones with 2-Azido-1,3-bis(2,6-diisopropylphenyl)imidazolium Hexafluorophosphate (IPrAP) 査読有り国際誌

Kitamura M., Ohtsuka K., Eto T., Tsuzaki M., Wada M., Shimooka H., Okauchi T.

Journal of Organic Chemistry 88 ( 21 ) 15494 - 15500 2023年11月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

The diazo-transfer reaction of nonactivated ketone under mild reaction conditions was developed. Various nonactivated ketones such as aryl methyl ketones, sec-alkyl methyl ketones, and cyclic ketones were transformed into their corresponding α-diazoketones in one step by treating 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP) in the presence of iPr2NH in ethylene glycol. In the reaction of IPrAP with prim-alkyl methyl ketone and prim-alkyl aryl ketones, migratory amidation proceeded under the reaction conditions to afford the corresponding amides.

DOI： 10.1021/acs.joc.3c01743

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Synthesis of an Ortho-Functionalized Tetrafluorinated Azobenzene Phosphoramidite for Incorporation into a Tetrafluorinated Azobenzene-Containing siRNA for Photocontrolled Gene Silencing 査読有り国際誌

Hammill M.L.(Ontario Tech University), Tsubaki K., Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

Current Protocols 3 ( 10 ) e874 2023年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

This article presents the detailed synthesis and characterization protocols for an ortho-functionalized tetrafluorinated azobenzene containing siRNA, which has photoswitchable properties. To design this tetrafluorinated azobenzene scaffold, several synthetic steps are performed to generate a symmetrical tetrafluorinated azobenzene diol. This diol is treated with dimethoxytrityl chloride (DMT-Cl) to protect one of the alcohols. Next, the DMT-protected tetrafluorinated monoalcohol is phosphitylated to afford the DMT-phosphoramidite building block used for solid-phase synthesis. This paper also contains the detailed biophysical characterization, biological testing, and photo-switching protocols of an ortho-functionalized fluorinated azobenzene containing siRNA (F-siRNA), which has photoswitchable properties that can be controlled with visible light. First, the F-siRNA was characterized by annealing the sense and antisense strands together and then measuring the circular dichroism (CD) profile and melting temperature (Tm) of the duplexes. Second, biological testing of the F-siRNA is performed in cell culture to determine their gene silencing efficacy. Finally, their gene-silencing activities are measured after exposure to green light to inactivate the F-siRNA, followed by blue light, which reactivates the F-siRNA. The F-siRNA can be kept inactive for up to 72 hr and reactivated at any time within this 72-hr window. © 2023 Wiley Periodicals LLC.

DOI： 10.1002/cpz1.874

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Formal synthesis of isoquinocyclinone using ortho-alkoxycarbonylmethylation of anthranol via diazoquinone 査読有り国際誌

Mitsuru Kitamura, Noriyuki Fukuzumi, Masayuki Shinagawa, Keiichiro Araki, Yutaro Shimizu, Shuhei Takahashi, Takumi Iwata, Hirokazu Shimooka, Tatsuo Okauchi

Tetrahedron Letters ( Elsevier ) 125 154618 2023年06月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

In this study, a formal synthesis of isoquinocyclinone is reported. Synthesis of key intermediate lactone 6, an intermediate in Koert's s total synthesis of isoquinocyclinone, was succeeded. The lactone 6 was synthesized by using our developed diazo-transfer reaction of anthranol with 2-azido-1,3-dimethylimidazolinium chloride (ADMC) and alkoxycarbonylmethylation of diazoquinone as key reactions.

DOI： 10.1016/j.tetlet.2023.154618

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Conversion of η<sup>4</sup>-(Vinylketene)iron complexes to η<sup>4</sup>-(Vinylketenimine)iron complexes using titanium chloride and amines 査読有り国際誌

Okauchi T., Teratani K., Nakagawa T., Ichimura T., Shimooka H., Kitamura M.

Journal of Organometallic Chemistry 990 2023年05月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

We developed a one-pot convenient method for the synthesis of η4-(vinylketenimine)iron complexes using η4-(vinylketene)iron complexes. This method does not require toxic reagents or prior preparation of corresponding reagents. The (vinylketene)iron complex is readily converted to (vinylketene)iron complex by mixing TiCl4 and a commercially available amine.

DOI： 10.1016/j.jorganchem.2023.122672

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Synthesis of Dinucleotide Non-Symmetrical Triester Phosphate Phosphoramidites and Their Incorporation Within Oligonucleotides 査読有り国際誌

Desaulniers, J.-P.(Ontario Tech University); Tsubaki, K.; Hammill, M. L.(Ontario Tech University); Kitamura, M.; Okauchi, T.

Current Protocols ( Willy ) 3 ( 5 ) e784 2023年05月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

In this protocol article, the synthesis of dinucleotide non-symmetrical triester phosphate phosphoramidites will be highlighted. Specifically, we use a selective transesterification starting with tris(2,2,2-trifluoroethyl) phosphate to afford a dinucleotide derivative phosphate ester. Substitution of the final trifluoroethyl group with various alcohols affords a dinucleotide triester phosphate with a hydrophobic group, which can then be deprotected and converted to a phosphoramidite for incorporation within oligonucleotides.

DOI： 10.1002/cpz1.784

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Synthesis, Derivatization and Photochemical Control of an ortho-Functionalized Tetrafluorinated Azobenzene-Modified siRNA 査読有り国際誌

Hammill M.L.(Ontario Tech University), Tsubaki K., Wang Y.(Ontario Tech University), Islam G.(Ontario Tech University), Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

ChemBioChem 23 ( 20 ) e202200386 2022年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

We report the synthesis of an ortho-functionalized tetrafluorinated azobenzene phosphoramidite for its site-specific incorporation into RNA. The tetrafluorinated azobenzene is embedded within the antisense strand of an siRNA duplex to form an ortho-functionalized tetrafluorinated azobenzene-containing siRNA (F-siRNAzo). The F-siRNAzo is inactivated via trans to cis conversion with green light (530 nm), and reactivated with blue light (470 nm) via cis to trans conversion in cell culture. The long half-life and stability of the tetrafluorinated azobenzene unit allows for reversible control of the F-siRNAzo in cell culture for up 72 hours.

DOI： 10.1002/cbic.202200386

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Formal Synthesis of Teadenols via Pd-catalyzed 6- endo Cyclization of Epoxyphenol 査読有り国際誌

Kitamura M., Suetake H., Hoshino K., Higashijima Y., Kisanuki M., Yuasa R., Yamaguchi Y., Shimazu T., Koga N., Hamada H., Miyori N., Shimooka H., Okauchi T.

Synlett 33 ( 15 ) 1523 - 1526 2022年08月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

Formal synthesis of teadenol A and B was achieved via Pd-catalyzed 6- endo cyclization of phenol having vinylepoxide moiety as a key reaction. Although 5- exo and 6- endo cyclizations compete for the cyclization of epoxides with a nucleophilic moiety at the 5-position, 6- endo cyclization can be realized by using a palladium catalyst.

DOI： 10.1055/a-1890-8287

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Synthesis of Diazoquinones and Azidophenols via Diazo-Transfer Reaction of Phenols 査読有り国際誌

Mitsuru Kitamura, Takashi Eto, Kazushige Konai, Shuhei Takahashi, Hirokazu Shimooka, Tatsuo Okauchi

European Journal of Organic Chemistry 2022 ( 18 ) 2022年04月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

An efficient diazo-transfer reaction of phenol is described. o-Quinone diazide (diazoquione) were synthesized from phenol by the diazo-transfer reaction using 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP), which is safe and stable crystalline, in MeOH in the presence of iPr2NH or DMAP. In addition, diazoquinones reacted with sodium azide smoothly in 2-methoxyethanol to give azidophenols in high yields.

DOI： 10.1002/ejoc.202200307

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SiRNAs with Neutral Phosphate Triester Hydrocarbon Tails Exhibit Carrier-Free Gene-Silencing Activity 査読有り国際誌

Matthew L. Hammill(Ontario Tech University), Kouta Tsubaki, Lidya Salim(Ontario Tech University), Andrew J. Varley(Ontario Tech University), Ifrodet Giorgees(Ontario Tech University), Mitsuru Kitamura, Tatsuo Okauchi, Jean-Paul Desaulniers(Ontario Tech University)

ACS Medicinal Chemistry Letters ( American Chemical Society ) 13 ( 4 ) 695 - 700 2022年04月

記述言語：英語掲載種別：研究論文（学術雑誌）

Short interfering RNAs (siRNAs) show promise as gene-silencing therapeutics, but their cellular uptake remains a challenge. We have recently shown the synthesis of siRNAs bearing a single neutral phenylethyl phosphotriester linkage within the sense strand. Here, we report the synthesis of siRNAs bearing three different hydrophobic phosphate triester linkages at key positions within the sense strand and assess their gene silencing in the absence of a transfection carrier. The best siRNAs bearing hydrophobic phosphate triester tails were not aromatic and exhibited effective gene silencing (IC50 ≈ 56–141 nM), whereas the aromatic derivative with three hydrophobic tails did not exhibit carrier-free gene silencing.

DOI： 10.1021/acsmedchemlett.2c00027

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New Phosphorylating Agents for the Synthesis of Phosphatidylethanolamines 査読有り国際誌

Tsubaki K., Yamanaka T., Hisamitsu T., Shimooka H., Kitamura M., Okauchi T.

Synthesis ( Thieme ) 53 ( 20 ) 3827 - 3835 2021年10月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

The preparation of three novel phosphorylating agents and their application toward the synthesis of phosphatidylethanolamines is described. These reagents are stable to air and moisture, and phosphorylate glycerols in good yield. The experimental procedures using these phosphorylating agents are simple. Moreover, the appropriate reagent can be selected based on the desired functional groups of the targeted phosphatidylethanolamine.

DOI： 10.1055/a-1516-9893

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Building siRNAs with Cubes: Synthesis and Evaluation of Cubane-Modified siRNAs 査読有り

Hammill M.L.(Ontario Tech University), Salim L.(Ontario Tech University), Tsubaki K., Varley A.J.(Ontario Tech University), Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

ChemBioChem 22 ( 20 ) 2981 - 2985 2021年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

Cubane molecules hold great potential for medicinal chemistry applications due to their inherent stability and low toxicity. In this study, we report the synthesis of a cubane derivative phosphoramidite for the incorporation of cubane into small interfering RNAs (siRNAs). Synthetic siRNAs rely on chemical modifications to improve their pharmacokinetic profiles. However, they are still able to mediate sequence-specific gene silencing via the endogenous RNA interference pathway. We designed a library of siRNAs bearing cubane at different positions within the sense and antisense strands. All siRNAs showed excellent gene-silencing activity, with IC50 values ranging from 45.4 to 305 pM. Incorporating the cubane modification in both the sense and antisense strand led to viable duplexes with good biological activity. To the best of our knowledge, this is the first report of siRNAs bearing a cubane derivative within the backbone.

DOI： 10.1002/cbic.202100334

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Pyrrole Formation via Reactivity of η4-(Vinylketenimine)iron Complexes with Electron-Deficient Alkynes 査読有り国際誌

Tatsuo Okauchi, Akihiro Urakawa, Nagomi Tabuchi, Miten Arai, Tomoya Nakagawa, Taiga Ichimura, Hirokazu Shimooka, Mitsuru Kitamura

Organometallics ( American Chemical Society ) 40 ( 17 ) 2929 - 2933 2021年08月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

When electron-deficient alkynes reacted with η4-(vinylketenimine)iron complexes, pyrroles were produced. Pyrrole formation involved the [2 + 3] cycloaddition of alkyne to the ketenimine moiety, migration of the vinyl group, and decomplexation. Either alkynes bearing two electron-withdrawing groups, or terminal alkynes with an electron-withdrawing group reacted to generate pyrroles.

DOI： 10.1021/acs.organomet.1c00321

その他リンク： https://pubs.acs.org/doi/10.1021/acs.organomet.1c00321

PdBr<inf>2</inf>-Catalyzed Acetal Formation of Carbonyl Compounds Using Diazophenanthrenequinone: Utility of 9,10-Phenanthrenedioxyacetal 査読有り国際誌

Kitamura M., Fujimura R., Nishimura T., Takahashi S., Shimooka H., Okauchi T.

European Journal of Organic Chemistry 2020 ( 33 ) 5319 - 5322 2020年09月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim We developed a new acetalization method of ketones and aldehydes under non-acidic conditions using diazophenanthrenequinone and PdBr2. The formed acetals that have a phenanthrene skeleton withstand under mild acidic conditions. Removal of acetals was successfully proceeded under strong acidic or oxidation conditions using aqueous ceric ammonium nitrate (CAN) to afford corresponding ketones and aldehydes.

DOI： 10.1002/ejoc.202000315

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Synthesis and Evaluation of Neutral Phosphate Triester Backbone-Modified siRNAs 査読有り国際誌

Tsubaki K., Hammill M.L.(Ontario Tech University), Varley A.J.(Ontario Tech University), Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

ACS Medicinal Chemistry Letters 11 ( 7 ) 1457 - 1462 2020年07月

記述言語：英語掲載種別：研究論文（学術雑誌）

Copyright © 2020 American Chemical Society. Two unsymmetrical dinucleotide phosphate triesters were synthesized via transesterification from tris(2,2,2-trifluoroethyl) phosphate. The protected triesters were phosphytilated to generate phosphoramidites for solid-phase oligonucleotide synthesis. Neutral phenylethyl phosphate-modified short-interfering RNAs (siRNAs) were synthesized and evaluated for their gene-silencing ability, siRNA strand selection, and resistance to nucleases. These backbone-modified phosphate triester siRNAs offer many improvements compared to natural unmodified siRNAs.

DOI： 10.1021/acsmedchemlett.0c00232

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85094628376&origin=inward

Rh(II)-catalyzed formal [3+3] cycloaddition of diazonaphthoquinones and propargyl alcohols: Synthesis of 2,3-dihydronaphtho-1,4-dioxin derivatives 査読有り国際誌

Kitamura M., Nishimura T., Otsuka K., Shimooka H., Okauchi T.

Tetrahedron Letters 61 ( 20 ) 2020年05月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 Elsevier Ltd A Rh(II)-catalyzed formal [3+3] cyclization of diazonaphthoquinones and propargyl alcohol is reported to afford 2,3-dihydro-1,4-benzodioxins. Various terminal propargyl alcohols react with diazonapthoquinone in the presence of Rh2(OAc)4 to give the corresponding dihydrodioxins in good to high yields. However, dihydrodioxins are not formed in the reaction of internal propargyl alcohols, and the O–H insertion product and 2,5-dihydrofurans are formed as the main product(s) depending on the terminal substituent. 2,3-Dihydro-1,4-benzodioxins are proposed to be formed via Rh(II)-catalyzed intermolecular oxonium ylide formation and subsequent 6-exo-dig cyclization with the internal alkynyl group.

DOI： 10.1016/j.tetlet.2020.151853

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九州工業大学工学部応用化学科の化学実験教育査読有り

中戸晃之, 竹中繁織, 岡内辰夫, 山村方人, 植田和茂

化学と教育 ( 公益社団法人日本化学会 ) 68 ( 3 ) 114 - 117 2020年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

<p>九州工業大学工学部応用化学科では，2年次前期より3年次後期にかけて，分析化学，物理化学，有機化学，化学工学・無機化学の順序で，学生実験を実施している。実験技術の習得に加え，エンジニアリングデザイン，コミュニケーション，チームワークなどの能力の涵養も目的としている。有機化学実験ではPBL（課題解決型学習）方式を取り入れており，学生アンケートや教員の実感では有効に機能していると考えられる。</p>

DOI： 10.20665/kakyoshi.68.3_114

その他リンク： https://ci.nii.ac.jp/naid/130007993107

Selective Transesterification of 2,2,2-Trifluoroethyl Phosphates: Synthesis of Mixed Unsymmetrical Phosphates 査読有り国際誌

Tsubaki K., Shimooka H., Kitamura M., Okauchi T.

Organic Letters 21 ( 23 ) 9779 - 9783 2019年12月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 American Chemical Society. A selective transesterification starting with tris(2,2,2-trifluoroethyl) phosphate has been developed. This method involves a three-step substitution for 2,2,2-trifluoroethoxy groups and enables the facile synthesis of mixed unsymmetric phosphate triesters from three different alcohols. The substitution of the trifluoroethoxy group at the phosphorus proceeds selectively in the presence of DBU or lithium alkoxides. This method can be applied for the preparation of phospholipids.

DOI： 10.1021/acs.orglett.9b04003

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85075667578&origin=inward

高校生のためのクロスカップリング実験（共著）

岡内辰夫,北村充

化学と教育 ( 日本化学会 ) 67 ( 3 ) 130 - 133 2019年03月

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