研究者詳細 - 北村　充

論文 - 北村　充

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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：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）

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

Kitamura M., Fukuzumi N., Shinagawa M., Araki K., Shimizu Y., Takahashi S., Iwata T., Shimooka H., Okauchi T.

Tetrahedron Letters 125 2023年07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）

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

Kitamura M., Eto T., Konai K., Takahashi S., Shimooka H., Okauchi T.

European Journal of Organic Chemistry 2022 ( 18 ) 2022年05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）

The first efficient diazo-transfer reaction of phenols is described. o-Quinone diazides (diazoquinones) were prepared from phenols in high yields by the diazo-transfer reaction using 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP, 2-PF6), which is a safe and stable crystalline. The reaction efficiently proceeded in methanol in the presence of a base. Phenols substituted with electron-donating groups reacted more smoothly than those having electron withdrawing groups. Reactive phenols were diazotized by IPrAP with iPr2NH as a base, and low reactive phenols were diazotized with N,N-dimethyl-4-aminopyridine (DMAP). Furthermore, the formed diazoquinones reacted with sodium azide in 2-methoxyethanol and afforded the corresponding azidophenol in high yields.

DOI： 10.1002/ejoc.202200307

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

Hammill M.L., Tsubaki K., Kitamura M., Okauchi T., Desaulniers J.P.

Current Protocols 3 ( 10 ) 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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Conversion of η4-(Vinylketene)iron complexes to η4-(Vinylketenimine)iron complexes using titanium chloride and amines 査読有り国際誌

Tatsuo Okauchi, Kohei Teratani, Tomoya Nakagawa, Taiga Ichimura, Hirokazu Shimooka, Mitsuru Kitamura

Journal of Organometallic Chemistry ( Elsevier B.V. ) 990 Article number 122672 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）

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

DOI： 10.1016/j.jorganchem.2023.122672

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

Desaulniers J.P., Tsubaki K., Hammill M.L., Kitamura M., Okauchi T.

Current Protocols 3 ( 5 ) 2023年05月

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. © 2023 Wiley Periodicals LLC. Basic Protocol 1: Synthesis of a DMT- and TBS-protected unsymmetrical dinucleotide. Basic Protocol 2: Synthesis of a DMT-protected unsymmetrical dinucleotide phosphotriester monoalcohols. Basic Protocol 3: Synthesis of DMT-protected phenylethyl phosphotriester dinucleotide phosphoramidites. Basic Protocol 4: Synthesis, purification, and characterization of RNAs containing triester phosphate modifications.

DOI： 10.1002/cpz1.784

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抗菌ペプチドの新たな機能と応用査読有り

ファラグヒシャム, 下岡弘和, 北村充

産業医大誌 ( 学校法人産業医科大学 ) 45 ( 1 ) 1 - 7 2023年03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）

<p>The emergent disaster of antimicrobial resistance developed by virulent bacteria has highlighted the need to investigate substitutes for the presently existing antibiotics. Antibacterial peptides (ABPs) have arisen as promising substitutes because of their unique killing effect on bacteria: bacterial resistance toward ABPs is negligible. ABPs have many beneficial subsidiary effects, such as protection of labile bioactive compounds, and they can be covalently connected to different materials to enhance their antibacterial effect. Many researchers have investigated many applications of these peptides recently, such as in a variety of pharmaceutical dosage forms and wastewater treatment.</p>

DOI： 10.7888/juoeh.45.1

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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 2023年01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）

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

Matthew L.Hammill, Kouta Tsubaki, Yuwei Wang, Golam Islam, Mitsuru Kitamura,Tatsuo Okauchi, Jean-Paul Desaulniers

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

DOI： 10.1002/cbic.202200386

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

Hammill M.L., Tsubaki K., Salim L., Varley A.J., Giorgees I., Kitamura M., Okauchi T., Desaulniers J.P.

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

Kitamura M., Hiroki S., 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01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）

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

Hammill M.L., Salim L., Tsubaki K., Varley A.J., Kitamura M., Okauchi T., Desaulniers J.P.

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

Okauchi T., Urakawa A., Tabuchi N., Arai M., Nakagawa T., Ichimura T., Shimooka H., Kitamura M.

Organometallics 40 ( 17 ) 2929 - 2933 2021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）

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

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New Phosphorylating Agents for the Synthesis of Phosphatidylethanolamines 査読有り

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

Synthesis (Germany) 53 ( 20 ) 3827 - 3835 2021年01月

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

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：責任著者記述言語：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

Tsubaki K., Hammill M.L., Varley A.J., Kitamura M., Okauchi T., Desaulniers J.P.

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

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Improvement of the novel inhibitor for Mycobacterium enoyl-acyl carrier protein reductase (InhA): a structure–activity relationship study of KES4 assisted by in silico structure-based drug screening 査読有り

Taira J., Umei T., Inoue K., Kitamura M., Berenger F., Sacchettini J.C., Sakamoto H., Aoki S.

Journal of Antibiotics 73 ( 6 ) 372 - 381 2020年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020, The Author(s), under exclusive licence to the Japan Antibiotics Research Association. InhA or enoyl-acyl carrier protein reductase of Mycobacterium tuberculosis (mtInhA), which controls mycobacterial cell wall construction, has been targeted in the development of antituberculosis drugs. Previously, our in silico structure-based drug screening study identified a novel class of compounds (designated KES4), which is capable of inhibiting the enzymatic activity of mtInhA, as well as mycobacterial growth. The compounds are composed of four ring structures (A–D), and the MD simulation predicted specific interactions with mtInhA of the D-ring and methylene group between the B-ring and C-ring; however, there is still room for improvement in the A-ring structure. In this study, a structure–activity relationship study of the A-ring was attempted with the assistance of in silico docking simulations. In brief, the virtual chemical library of A-ring-modified KES4 was constructed and subjected to in silico docking simulation against mtInhA using the GOLD program. Among the selected candidates, we achieved synthesis of seven compounds, and the bioactivities (effects on InhA activity and mycobacterial growth and cytotoxicity) of the synthesized molecules were evaluated. Among the compounds tested, two candidates (compounds 3d and 3f) exhibited superior properties as mtInhA-targeted anti-infectives for mycobacteria than the lead compound KES4.

DOI： 10.1038/s41429-020-0293-6

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Structural modification of a novel inhibitor for mycobacterium enoyl-acyl carrier protein reductase assisted by in silico structure-based drug screening 査読有り

Taira J., Nagano T., Kitamura M., Yamaguchi M., Sakamoto H., Aoki S.

International Journal of Mycobacteriology 9 ( 1 ) 12 - 17 2020年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 Medknow. All rights reserved. Background: Mycobacterium tuberculosis enoyl-acyl carrier protein reductase (mtInhA) is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls, and has been targeted in the development of anti-tuberculosis (TB) drugs. In our previous in silico structure-based drug screening study, we identified KES4, a novel class of mtInhA inhibitor. KES4 is composed of four ring structures (A-D-rings) and molecular dynamic simulation predicted that the D-ring is essential for the interaction with mtInhA. Methods: The structure-activity relationship study of the D-ring was attempted and aided by in silico docking simulations to improve the mtInhA inhibitory activity of KES4. A virtual chemical library of the D-ring-modified KES4 was then constructed and subjected to in silico docking simulation against mtInhA using the GOLD program. The candidate compound showing the highest GOLD score, referred to as KEN1, was synthesized, and its biological properties were compared with those of the lead compound KES4. Results: We achieved the synthesis of KEN1 and evaluated its effects on InhA activity, mycobacterial growth, and cytotoxicity. The antimycobacterial activity of KEN1 was comparable to that of the lead compound (KES4), although it exhibited superior activity in mtInhA inhibition. \Conclusions: We obtained a KES4 derivative with high mtInhA inhibitory activity by in silico docking simulation with a chemical library consisting of a series of D-ring-modified KES4.

DOI： 10.4103/ijmy.ijmy_184_19

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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

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

Tetrahedron Letters 61 ( 20 ) 2020年01月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 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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Selective Transesterification of 2,2,2-Trifluoroethyl Phosphates: Synthesis of Mixed Unsymmetrical Phosphates 査読有り

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

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

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

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