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Inovation in fluorous chemistry focusing on selective analysis of peptides and proteins

Research Project

Project/Area Number 26410166
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Analytical chemistry
Research InstitutionFukuoka University

Principal Investigator

Nohta Hitoshi  福岡大学, 薬学部, 教授 (20164668)

Co-Investigator(Renkei-kenkyūsha) YAMAGUCHI Masatoshi  福岡大学, 薬学部, 教授 (50117280)
HAYAMA Tadashi  福岡大学, 薬学部, 准教授 (90549693)
Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Keywordsフルオラス化学 / 前処理 / ペプチド / タンパク質 / 誘導体化 / アミノ基 / リン酸基 / ペプチド分析 / タンパク質分析 / パーフルオロアルキル / LC/MS/MS / パーフルオラス化合物 / フルオラスカラム / 分析化学 / フルオラスケミストリー / 分離分析 / 液体クロマトグラフィー / 金属キレートアフィニティー / 溶媒・固相抽出
Outline of Final Research Achievements

Highly selective and effective purification methods for peptides and proteins have been developed. One is for polyamino-containing peptides. The amino moieties of peptides are perfluoroalkylated with amine-reactive fluorous reagent, then the derivatives are highly selectively extracted to a fluorous solvent, followed by LC/MS/MS analysis. The other is for phosphorylated peptides. The Fe(III) immobilized fluorous reagent is designed and synthesized. The reagent reacts with phosphorylated peptides to form their fluorous chelates, those are extracted selectively into a fluorous solvent. The former is applied to the determination of brain peptides in rat brain samples, and the latter to the assay for protein kinase activity.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (41 results)

All 2018 2017 2016 2015 2014

All Journal Article (15 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 12 results,  Open Access: 8 results) Presentation (26 results) (of which Int'l Joint Research: 3 results,  Invited: 1 results)

  • [Journal Article] Fluorous-assisted Metal Chelate Affinity Extraction for Nucleotides Followed by HILIC-MS Analysis2018

    • Author(s)
      Ena Kiyokawa, Tadashi Hayama, Hideyuki Yoshida, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Journal of Chromatography B

      Volume: 1074-1075 Pages: 86-90

    • DOI

      10.1016/j.jchromb.2017.12.036

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Assessment of Anticancer Drug Effects on Pancreatic Cancer Cells under Glucose-Depleted Conditions Using Intracellular and Extracellular Amino Acid Metabolomics2018

    • Author(s)
      Ryoko Tomita, Kenchiro Todoroki, Tadashi Hayama, Hideyuki Yoshida, Toshihiro Fujioka, Manabu Nakashima, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Biological and Pharmaceutical Bulletin

      Volume: 41 Issue: 2 Pages: 220-228

    • DOI

      10.1248/bpb.b17-00746

    • NAID

      130006329269

    • ISSN
      0918-6158, 1347-5215
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Multi-Perfluoroalkyl Derivatization of Polyamines for Selective Liquid Chromatography-Tandem Mass Spectrometric Analysis Utilizing Fluorous Affinity2017

    • Author(s)
      Tadashi Hayama, Erina Tamashima, Hideyuki Yoshida, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      CHROMATOGRAPHY

      Volume: 38 Issue: 3 Pages: 107-113

    • DOI

      10.15583/jpchrom.2017.012

    • NAID

      130007040470

    • ISSN
      1342-8284, 1348-3315
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fluorous-assisted metal chelate affinity extraction technique for analysis of protein kinase activity2016

    • Author(s)
      Tadashi Hayama, Ena Kiyokawa, Hideyuki Yoshida, Osamu Imakyure, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Talanta

      Volume: 156/157 Pages: 1-5

    • DOI

      10.1016/j.talanta.2016.04.058

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Amino Acid Metabolomics Using LC-MS/MS: Assessment of Cancer-Cell Resistance in a Simulated Tumor Microenvironment2016

    • Author(s)
      Ryoko Tomita, Kenichiro Todoroki, Hiroshi Maruoka, Hideyuki Yoshida, Toshihiro Fujioka, Manabu Nakashima, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Analytical Sciences

      Volume: 32 Issue: 8 Pages: 893-900

    • DOI

      10.2116/analsci.32.893

    • NAID

      130005256428

    • ISSN
      0910-6340, 1348-2246
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Selective HPLC Analysis of Polycylic Aromatic Hydrocarbons Using Exciplex Fluorescence Phenomenon2016

    • Author(s)
      轟木堅一郎,柳郷恵子,吉田秀幸,能田均,山口政俊
    • Journal Title

      BUNSEKI KAGAKU

      Volume: 65 Issue: 12 Pages: 729-735

    • DOI

      10.2116/bunsekikagaku.65.729

    • NAID

      130005286334

    • ISSN
      0525-1931
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Direct Tandem Mass Spectrometric Analysis of Amino Acids in Plasma Using Fluorous Derivatization and Monolithic Solid-phase Purification2015

    • Author(s)
      Erina Tamashima, Tadashi Hayama, Hideyuki Yoshida, Osamu Imakyure, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Journal of Pharmaceutical and Biomedical Analysis

      Volume: 115 Pages: 201-207

    • DOI

      10.1016/j.jpba.2015.07.008

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective and sensitive liquid chromatographic determination method of 5-hydroxyindoles with fluorous and fluorogenic derivatization2015

    • Author(s)
      Yohei Sakaguchi, Jun Ikenaga, Hideyuki Yoshida, Tadashi Hayama, Miki Itoyama, Kenichiro Todoroki, Osamu Imakyure, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Journal of Pharmaceutical and Biomedical Analysis

      Volume: 114 Pages: 348-354

    • DOI

      10.1016/j.jpba.2015.06.003

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective Extraction of Nucleotides with Fluorous Biphasic System Utilizing Perfluoroalkylamine as an Ion-pair Reagent2015

    • Author(s)
      Tadashi Hayama, Ena Kiyokawa, Hideyuki Yoshida, Osamu Imakyure, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Chromatography

      Volume: 36 (1) Issue: 1 Pages: 13-18

    • DOI

      10.15583/jpchrom.2015.001

    • NAID

      130005069043

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] フルオラスの選択性を利用した細胞試料中ヌクレオチド類の金属キレートアフィニティー抽出2014

    • Author(s)
      巴山 忠,薬師寺寿世,川見祐介,糸山美紀,吉田秀幸,能田 均,山口政俊
    • Journal Title

      Chromatography

      Volume: 35sup2 Pages: 21-21

    • Related Report
      2014 Research-status Report
  • [Journal Article] Liquid Chromatography-tandem Mass Spectrometry with Fluorous Derivatization Method for Selective Analysis of Sialyl Oligosaccharides2014

    • Author(s)
      Yohei Sakaguchi, Tadashi Hayama, Hideyuki Yoshida, Miki Itoyama, Kenichiro Todoroki, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Rapid Communication in Mass Spectrometry

      Volume: 28 (23) Issue: 23 Pages: 2481-2489

    • DOI

      10.1002/rcm.7042

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Assessment of the Efficacy of Anticancer Drugs by Amino Acid Metabolomics Using Fluorescence Derivatization-HPLC2014

    • Author(s)
      Ryoko Tomita, Kenichiro Todoroki, Kazuyuki Machida, Sho Nishida, Hiroshi Maruoka, Hideyuki Yoshida, Toshihiro Fujioka, Manabu Nakashima, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Analytical Sciences

      Volume: 30 Issue: 7 Pages: 751-758

    • DOI

      10.2116/analsci.30.751

    • NAID

      130004442316

    • ISSN
      0910-6340, 1348-2246
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fluorous Affinity-based Separation Techniques for the Analysis of Biogenic and Related Molecules2014

    • Author(s)
      Tadashi Hayama, Hideyuki Yoshida, Masatoshi Yamaguchi, Hitoshi Nohta
    • Journal Title

      Journal of Pharmaceutical and Biomedical Analysis

      Volume: 101 (1) Pages: 151-160

    • DOI

      10.1016/j.jpba.2014.04.035

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] フルオラス-金属キレートアフィニティー試薬を用いたリン酸基含有化合物の選択的抽出法の開発2014

    • Author(s)
      巴山 忠、井上裕也、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Journal Title

      Chromatography

      Volume: 35sup1 Pages: 107-108

    • Related Report
      2014 Research-status Report
  • [Journal Article] モノリス型フルオラス固相カラムを用いたパーフルオロアルキルアミノ酸の精製とLC-MS/MS分析2014

    • Author(s)
      玉嶋江莉奈、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Journal Title

      Chromatography

      Volume: 35sup1 Pages: 61-62

    • Related Report
      2014 Research-status Report
  • [Presentation] LC-MS/MS Analysis of Peptides in Brain with Fluorous Derivatization2018

    • Author(s)
      ○Ena Kiyokawa, Reiko Koga, Tadashi Hayama, Hideyuki Yoshida, Masatoshi Yamaguchi, Hitoshi Nohta
    • Organizer
      The 45th International Symposium on High Performance Liquid Phase Separations and Related Techniques
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 金属固定化フルオラス試薬を用いたリン脂質の選択的抽出法の開発2017

    • Author(s)
      清川恵奈,巴山忠,川見祐介,吉田秀幸,山口政俊,能田均
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台市
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] 生理活性ペプチドのフルオラス誘導体化LC-MS/MS分析2017

    • Author(s)
      ○梶山彩乃,清川恵奈,巴山忠,吉田秀幸,山口政俊,能田均
    • Organizer
      第54回化学関連支部合同九州大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 三次元HPLCを用いる生体内シトルリン鏡像異性体の高選択的分析法開発2017

    • Author(s)
      ○古賀鈴依子,門田靖彦,西尾康弘,三田真史,清川恵奈,吉田秀幸,山口政俊,能田均,浜瀬健司
    • Organizer
      第30回バイオメディカル分析科学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] オンライン-フルオラス誘導体化によるクルクミンの高感度LC-MS/MS分析2017

    • Author(s)
      ○清川恵奈,竹下阿紗子,巴山忠,古賀鈴依子,吉田秀幸,山口政俊,能田均
    • Organizer
      日本分析化学会第66年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] UPLC-UV分析によるアミノ酸メタボロミクス(2)2017

    • Author(s)
      ○冨田陵子,黒木由紀,轟木堅一郎,巴山忠,吉田秀幸,中島学,能田均,山口政俊,藤岡稔大
    • Organizer
      日本分析化学会第66年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] パーフルオロポリエーテルカルボン酸を用いたリン脂質のフルオラス金属キレートアフィニティー抽出2017

    • Author(s)
      ○清川恵奈,田坂友里恵,巴山忠,古賀鈴依子,吉田秀幸,山口政俊,能田均
    • Organizer
      第28回クロマトグラフィー科学会議
    • Related Report
      2017 Annual Research Report
  • [Presentation] 脳内ペプチド類の選択的LC-MS/MS分析法の開発とマウス脳組織への応用2016

    • Author(s)
      清川恵奈,久保田桃子,巴山忠,川見祐介,吉田秀幸,山口政俊,能田均
    • Organizer
      33回日本薬学会九州支部大会
    • Place of Presentation
      鹿児島市
    • Year and Date
      2016-12-03
    • Related Report
      2016 Research-status Report
  • [Presentation] nalysis of protein kinase activity with fluorous-assisted metal chelate affinity extraction of phosphopeptide followed by fluorescence detection2016

    • Author(s)
      KIYOKAWA Ena, HAYAMA Tadashi, YOSHIDA Hideyuki, IMAKYURE Osamu, YAMAGUCHI Masatoshi, NOHTA Hitosh
    • Organizer
      International Symposium on Luminescence Spectrometry
    • Place of Presentation
      Taipei, Taiwan
    • Year and Date
      2016-11-22
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Fluorous derivatization technique for selective analysis of biogenic-related compounds with HPLC-fluorescence detection2016

    • Author(s)
      HAYAMA Tadashi, YOSHIDA Hideyuki, SAKAGUCHI Yohei, IKENAGA Jun, TODOROKI Kenichiro, YAMAGUCHI Masatoshi, NOHTA Hitoshi
    • Organizer
      International Symposium on Luminescence Spectrometry
    • Place of Presentation
      Taipei, Taiwan
    • Year and Date
      2016-11-22
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] マルチフルオラス誘導体化による脳内ペプチド類の選択的LC-MS/MS分析2016

    • Author(s)
      久保田桃子,清川恵奈,巴山忠,川見祐介,吉田秀幸,山口政俊,能田均
    • Organizer
      第34回九州分析化学若手の会夏季セミナー
    • Place of Presentation
      大分県日田市
    • Year and Date
      2016-07-29
    • Related Report
      2016 Research-status Report
  • [Presentation] アポトーシス誘導Jurkat細胞中物ヌクレオチド類の選択的抽出とその定量的解析2016

    • Author(s)
      清川恵奈、巴山 忠、相川晃慶、川見祐介、糸山美紀、小迫知弘、吉田秀幸、添田秦司、山口政俊、能田 均
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2016-03-29
    • Related Report
      2015 Research-status Report
  • [Presentation] Ion-pair fluorous biphasic extraction及びHILICによるヌクレオチド類の選択的分析法開発2015

    • Author(s)
      清川恵奈、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Organizer
      第13回次世代を担う若手のためのフィジカル・ファーマフォーラム
    • Place of Presentation
      長崎(ホテル清風)
    • Year and Date
      2015-08-20
    • Related Report
      2015 Research-status Report
  • [Presentation] フルオラス相互作用を利用したアミノ酸のタンデムマス分析と病態モデ ルマウス試料への適2015

    • Author(s)
      玉嶋江莉奈、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Organizer
      第13回次世代を担う若手のためのフィジカル・ファーマフォーラム
    • Place of Presentation
      長崎(ホテル清風)
    • Year and Date
      2015-08-20
    • Related Report
      2015 Research-status Report
  • [Presentation] フルオラス-金属キレートアフィニティー抽出を利用したプロテインキナーゼ活性の蛍光測定2015

    • Author(s)
      長野元貴、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Organizer
      第33回九州分析化学若手の会 夏季セミナー
    • Place of Presentation
      天草(亀屋ホテル)
    • Year and Date
      2015-07-24
    • Related Report
      2015 Research-status Report
  • [Presentation] フルオラスイオンペア抽出法によるヌクレオチド類の選択的分析と白血病由来細胞試料への適用2015

    • Author(s)
      清川恵奈、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Organizer
      第22回クロマトグラフィーシンポジウム
    • Place of Presentation
      近畿大学 東大阪キャンパス
    • Year and Date
      2015-05-29
    • Related Report
      2015 Research-status Report
  • [Presentation] LC-MS/MSによるアミノ酸メタボロミクス ー低酸素・栄養飢餓状態で培養した大腸がん細胞DLD1についてー2015

    • Author(s)
      冨田陵子、西田 翔、巴山 忠、轟木堅一郎、吉田秀幸、丸岡 博、中島 学、能田 均、山口政俊、藤岡稔大
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] フルオラスの選択性を利用した細胞試料中ヌクレオチド類の金属キレートアフィニティー抽出2014

    • Author(s)
      巴山 忠,薬師寺寿世,川見祐介,糸山美紀,吉田秀幸,能田 均,山口政俊
    • Organizer
      第25回クロマトグラフィー科学会議
    • Place of Presentation
      京都
    • Year and Date
      2014-12-12
    • Related Report
      2014 Research-status Report
  • [Presentation] 亜鉛固定化Krytoxを利用したテトラサイクリン系薬剤の選択的フルオラス二相系抽出2014

    • Author(s)
      古森貴子,清川恵奈,巴山 忠,川見祐介,糸山美紀,吉田秀幸,能田 均,山口政俊
    • Organizer
      第31回日本薬学会九州支部大会
    • Place of Presentation
      福岡
    • Year and Date
      2014-12-06
    • Related Report
      2014 Research-status Report
  • [Presentation] 金属固定化フルオラス試薬を利用したテトラサイクリン系抗生物質の選択的抽出法の開発2014

    • Author(s)
      清川恵奈,古森貴子,巴山 忠,川見祐介,糸山美紀,吉田秀幸,能田 均,山口政俊
    • Organizer
      第27回バイオメディカル分析科学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-08-20
    • Related Report
      2014 Research-status Report
  • [Presentation] ジルコニア-リン酸基間の特異的親和性を利用した分離指向性誘導体化法の開発2014

    • Author(s)
      大塚恵未、川見祐介、糸山美紀、巴山 忠、吉田秀幸、能田 均、山口政俊
    • Organizer
      第32回九州分析化学若手の会 夏季セミナー
    • Place of Presentation
      北九州
    • Year and Date
      2014-07-25
    • Related Report
      2014 Research-status Report
  • [Presentation] マイケル付加反応を介したクルクミンのフルオラス誘導体化と選択的HPLC分析2014

    • Author(s)
      林英里奈、寺崎友理、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Organizer
      第32回九州分析化学若手の会 夏季セミナー
    • Place of Presentation
      北九州
    • Year and Date
      2014-07-24
    • Related Report
      2014 Research-status Report
  • [Presentation] フルオラス誘導体化LC-MS3によるバソプレシンの高感度かつ高選択的分析法の開発2014

    • Author(s)
      竹下理紗、玉嶋江莉奈、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Organizer
      第32回九州分析化学若手の会 夏季セミナー
    • Place of Presentation
      北九州
    • Year and Date
      2014-07-24
    • Related Report
      2014 Research-status Report
  • [Presentation] イミノ二酢酸型フルオラス試薬を利用したリン酸基含有化合物の金属キレートアフィニティー/フルオラス二相系抽出2014

    • Author(s)
      薬師寺寿世、濱古賀好、巴山 忠、川見祐介、糸山美紀、吉田秀幸、能田 均、山口政俊
    • Organizer
      第32回九州分析化学若手の会 夏季セミナー
    • Place of Presentation
      北九州
    • Year and Date
      2014-07-24
    • Related Report
      2014 Research-status Report
  • [Presentation] フルオラス-金属キレートアフィニティー試薬を用いたリン酸基含有化合物の選択的抽出法の開発2014

    • Author(s)
      巴山 忠,井上裕也,川見祐介,糸山美紀,吉田秀幸,能田 均,山口政俊
    • Organizer
      第21回クロマトグラフィーシンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2014-06-05
    • Related Report
      2014 Research-status Report
  • [Presentation] モノリス型フルオラス固相カラムを用いたパーフルオロアルキル化アミノ酸の選択的抽出とLC-MS/MS分析2014

    • Author(s)
      玉嶋江莉奈,巴山 忠,川見祐介,糸山美紀,吉田秀幸,能田 均,山口政俊
    • Organizer
      第21回クロマトグラフィーシンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2014-06-05
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2019-03-29  

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