研究者詳細 - 布施　新一郎

論文 - 布施　新一郎

分割表示 69 件中 21 - 40 件目／全件表示 >>

Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution 査読有り

Hisashi Masui, Sena Kanda, Shinichiro Fuse

Communications Chemistry 6 巻頁： 47 2023年3月

A liquid-phase continuous-flow peptide synthesizer for preparing C-terminal free peptides 査読有り

Yuma Otake, Kyohei Adachi, Yoshiaki Yamashita, Natsumi Iwanaga, Hirokatsu Sunakawa, Taiki Shamoto, Jun-ichi Ogawa, Atsushi Ito, Yutaka Kobayashi, Keiichi Masuya, Shinichiro Fuse, Daisuke Kubo, Hidenosuke Itoh

Reaction Chemistry & Engineering 8 巻 ( 4 ) 頁： 863 - 870 2022年12月

Micro-flow N-acylation using highly electrophilic acyl ammonium cations for peptide and urethane-protected N-carboxyanhydride syntheses 招待有り査読有り

Hisashi Masui, Shinichiro Fuse

Journal of Synthetic Organic Chemistry, Japan 80 巻 ( 11 ) 頁： 986 - 993 2022年11月

Sequential Nucleophilic Substitution of Phosphorus Trichloride with Alcohols in a Continuous-Flow Reactor and Consideration of a Mechanism for Reduced Over-reaction through the Addition of Imidazole 査読有り

Hiroshi Kitamura, Yuma Otake, Naoto Sugisawa, Hiroki Sugisawa, Tomonori Ida, Hiroyuki Nakamura, Shinichiro Fuse

CHEMISTRY-A EUROPEAN JOURNAL 28 巻 ( 37 ) 頁： e202200932 2022年7月

Recent Advances in the Solid- and Solution-Phase Synthesis of Peptides and Proteins Using Microflow Technology 招待有り査読有り

Masui Hisashi, Fuse Shinichiro

ORGANIC PROCESS RESEARCH & DEVELOPMENT 26 巻 ( 6 ) 頁： 1751 - 1765 2022年6月

担当区分：最終著者,　責任著者記述言語：日本語出版者・発行元：Organic Process Research and Development

Peptides have become increasingly important as drugs and drug candidates. In particular, specialty peptides have garnered considerable attention in recent years because of their improved metabolic stability, higher affinity, and biological target selectivity; some of them have the ability to enable cell membrane permeation and oral administration. Despite its long history, peptide synthesis has various limitations, such as high cost, generation of large amounts of waste, and the requirement for hazardous reagents and solvents. Microflow synthesis, wherein the inner diameter of the reaction tube is ≤1 mm, presents several advantages compared with conventional batch synthesis, such as precise control of the reaction time on a short scale, precise reaction temperature control, and facile scale-up with high reproducibility. Microflow technology has been utilized for peptide synthesis since the beginning of the 21st century. The advantages of microflow synthesis enable the use of highly active and unstable chemical species or high-Temperature conditions that accelerate peptide synthesis. The combined use of microflow technology, automated synthesis, and online monitoring technologies has emerged in recent years. This approach not only improved the synthetic efficiency but also afforded large amounts of reliable data that can be used to train machine learning models. This review summarizes the solid-and solution-phase syntheses of α-peptides and specialty peptides, including N-methylated peptides, β-peptides, and cyclic peptides, reported mainly after 2017. The recently reported mesoflow peptide syntheses (inner diameter of the reaction channels > 1 mm), the microflow automated syntheses, and in-line analysis are covered in this review.

DOI： 10.1021/acs.oprd.2c00074

Web of Science

Scopus

A micro-flow rapid dual activation approach for urethane-protected alpha-amino acid N-carboxyanhydride synthesis 査読有り

Okabe Ren, Sugisawa Naoto, Fuse Shinichiro

ORGANIC & BIOMOLECULAR CHEMISTRY 20 巻 ( 16 ) 頁： 3303 - 3310 2022年3月

Continuous-Flow Synthesis of N-Methylated Peptides via Generation of an Acyl N-Methylimidazolium Cation.

Masui H, Fuse S

Chemical Protein Synthesis 2530 巻頁： 45 - 53 2022年

記述言語：英語出版者・発行元：Methods in Molecular Biology

A detailed protocol is described for the continuous-flow synthesis of N-methylated peptides. N-Methylated peptides are very important class of bioactive compounds compared with normal peptides because they can enhance oral bioavailability, cell membrane permeability, and stability against enzymatic degradation. In our developed flow synthesis, a variety of N-methylated dipeptides is obtained in high yields without severe racemization from equivalent amounts of amino acids. The addition of a strong Brønsted acid is critical to generate the highly reactive N-methylimidazolium cation species to accelerate the amidation. The developed approach enabled the synthesis of a bulky peptide with a higher yield in a shorter amount of time compared with the results of conventional amidation.

DOI： 10.1007/978-1-0716-2489-0_4

Scopus

PubMed

Rapid and mild one-flow synthetic approach to unsymmetrical sulfamides guided by Bayesian optimization 査読有り国際共著

Naoto Sugisawa, Hiroki Sugisawa, Yuma Otake, Roman V. Krems, Hiroyuki Nakamura, Shinichiro Fuse

Chemistry -Methods 1 巻 ( 11 ) 頁： 484 - 490 2021年8月

有機合成化学は面白い！

布施新一郎

有機合成化学協会誌 79 巻 ( 4 ) 頁： 346 - 348 2021年4月

Rapid and mild lactamization using highly electrophilic triphosgene in a micro-flow reactor, 査読有り

Shinichiro Fuse, Keiji Komuro, Yuma Otake, Hisashi Masui, Hiroyuki Nakamura

Chemistry a European Journal 27 巻 ( 27 ) 頁： 7525 - 7532 2021年1月

Cluster Preface: Integrated Synthesis Using Continuous-Flow Technologies 招待有り

Fuse Shinichiro

SYNLETT 31 巻 ( 19 ) 頁： 1878 - 1879 2020年12月

Recent Advances in Continuous-Flow Reactions Using Metal-Free Homogeneous Catalysts 招待有り査読有り

Naoto Sugisawa, Hiroyuki Nakamura, Shinichiro Fuse

Catalysts 10 巻 ( 11 ) 頁： 1321 2020年11月

マイクロフロー合成法を駆動力とするペプチド合成の革新

布施新一郎

MEDCHEM NEWS 30 巻 ( 4 ) 頁： 193 - 200 2020年11月

記述言語：日本語出版者・発行元：公益社団法人日本薬学会

<p>ペプチド医薬品はその重要性を増しており、特に近年では、環状ペプチドや<i>N</i>-メチル化ペプチドを含む特殊ペプチドが注目を集めている。一方で、これらペプチドの低コスト生産の実現は未だ道半ばである。Theodor Curtiusによる初のペプチド結合形成の報告から140年近くの歳月が経過し、すでに無数の合成法が開発されてきた中でペプチド合成に革新を起こすことは極めて挑戦的な課題といえる。1990年代半ばに登場した、微小な流路を反応場とするマイクロフロー合成法は、これまでのバッチリアクターの利用を基盤とする合成法では制御困難な反応に新たな価値を付与するものである。本稿ではペプチド合成に革新を起こすべく推進してきた、マイクロフロー合成法を駆使したアミド化反応の開発について紹介する。</p>

DOI： 10.14894/medchem.30.4_193

CiNii Research

Size-Controllable and Scalable Production of Liposomes Using a V-Shaped Mixer Micro-Flow Reactor

Kawamura Jun, Kitamura Hiroshi, Otake Yuma, Fuse Shinichiro, Nakamura Hiroyuki

ORGANIC PROCESS RESEARCH & DEVELOPMENT 24 巻 ( 10 ) 頁： 2122 - 2127 2020年10月

記述言語：日本語出版者・発行元：Organic Process Research and Development

The use of microfluidics has been regarded as a promising solution for the costly and complex preparation of liposomes, and the development of controllable and scalable liposome production using simple-structured, readily available, and inexpensive "off-the-shelf"microfluidics remains important pursuit. We have achieved simple and inexpensive production of liposomes using an off-the-shelf V-shaped mixer. The size of liposomes was controlled (50-70 nm diameter, PDI < 0.1) in the desired range (<100 nm) by changing the relative flow rate of the ethanol solution of lipids and the aqueous solution. The developed approach is scalable (12 mL/min), and several representative lipids, including inexpensive Span 60, can be used for the preparation of nanoparticles.

DOI： 10.1021/acs.oprd.0c00174

Web of Science

Scopus

Size-controllable and scalable production of liposomes using a V-shape mixer micro-flow reactor 招待有り査読有り

Jun Kawamura, Hiroshi Kitamura, Yuma Otake, Shinichiro Fuse, Hiroyuki Nakamura

Organic Process Research and Development 24 巻 ( 10 ) 頁： 2122 - 2127 2020年6月

Investigation into the influence of an acrylic acid acceptor in organic D-π-A sensitizers against phototoxicity 査読有り

Shinichiro Fuse, Wataru Moriya, Shinichi Sato, Hiroyuki Nakamura

Bioorganic and Medicinal Chemistry 28 巻 ( 13 ) 頁： 115558 2020年5月

Photochemical Conversion of Isoxazoles to 5-Hydroxyimidazolines. 査読有り

Morita T, Fuse S, Nakamura H

Organic letters 22 巻 ( 9 ) 頁： 3460 - 3463 2020年5月

N-Methylated Peptide Synthesis via Acyl N-Methylimidazolium Cation Generation Accelerated by a Brønsted Acid. 査読有り

Yuma Otake, Yusuke Shibata, Yoshihiro Hayashi, Susumu Kawauchi, Hiroyuki Nakamura, Shinichiro Fuse

Angewandte Chemie (International ed. in English) 59 巻 ( 31 ) 頁： 12925 - 12930 2020年4月

Micro-flow synthesis of β-amino acid derivatives via a rapid dual activation approach. 査読有り

Naoto Sugisawa, Hiroyuki Nakamura, Shinichiro Fuse

Chemical communications (Cambridge, England) 56 巻頁： 4527 - 4530 2020年4月

Single-Step, Rapid, and Mild Synthesis of beta-Amino Acid N-Carboxy Anhydrides Using Micro-Flow Technology

Sugisawa Naoto, Otake Yuma, Nakamura Hiroyuki, Fuse Shinichiro

CHEMISTRY-AN ASIAN JOURNAL 15 巻 ( 1 ) 頁： 79 - 84 2020年1月

記述言語：日本語出版者・発行元：Chemistry - An Asian Journal

β-Amino acid N-carboxy anhydrides (β-NCAs) are rarely used in the synthesis of β-peptides, which is due mainly to the poor availability of these potentially useful substrates. Herein, we describe the heretofore challenging synthesis of β-NCAs via a single-step, rapid, and mild formation using pH flash switching and flash dilution, which are aspects of micro-flow technology. We synthesized 15 β-NCAs in good to excellent yields that included acid-labile β-NCAs that cannot be readily synthesized using the conventional Leuchs approach. Scaled-up synthesis using this process can be readily achieved via continuous operation.

DOI： 10.1002/asia.201901429

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論文 - 布施 新一郎

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論文 - 布施　新一郎