Preparation and Structure of Elastin Crosslinkers and Development of COPD Diagnosis

• Project/Area Number: 25750388
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Biomolecular chemistry
• Research Institution: Sophia University
• Principal Investigator: USUKI Toyonobu 上智大学, 理工学部, 准教授 (50514535)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2015: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000); Fiscal Year 2014: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2013: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
• Keywords: バイオマーカー / エラスチン / desmosine / COPD

Outline of Final Research Achievements

In this study, synthesis of elastin crosslinkers and COPD biomarkers desmosine and isodesmosine was achieved via a lanthanide-promoted Chichibabin pyridine synthesis as a key step. Isotopically labeled desmosines were also prepared for the use of an internal standard in LC-MS analysis of desmosines. In addition, preparation of cyclic desmosine was succeeded.

Research Products

• [Int'l Joint Research] Mount Sinai School of Medicine(米国)
• [Int'l Joint Research] Chinese University of Hong Kong(China)
• [Journal Article] Synthesis and SAR of 4-methyl-5-penthylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum (2016)
  • Author(s): Chihiro Murata, Tetsuhiro Ogura, Shuhei Narita, Anna P. Kondo, Natsumi Iwasaki, Tamao Saito, Toyonobu Usuki
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 26 Issue: 5 Pages: 1428-1433
  • DOI: 10.1016/j.bmcl.2016.01.067
  • Peer Reviewed
• [Journal Article] Total Synthesis of Isodesmosine via Stepwise, Regioselective Negishi and Sonogashira Cross-Coupling Reactions (2015)
  • Author(s): Yohei Koseki, Takanori Sugimura, Keita Ogawa, Rina Suzuki, Haruka Yamada, Noriyuki Suzuki, Yoshiro Masuyama, Yong Y. Lin, Toyonobu Usuki
  • Journal Title: European Journal of Organic Chemistry Volume: 18 Issue: 18 Pages: 4024-4032
  • DOI: 10.1002/ejoc.201500449
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Ionic Liquid-Mediated Extraction of Bilobalide from Ginkgo biloba Leaves (2015)
  • Author(s): Shingo Onda, Toyonobu Usuki, Masahiro Yoshizawa-Fujita, Masahiro Rikukawa
  • Journal Title: Chemistry Letters Volume: 44 Issue: 11 Pages: 1461-1463
  • DOI: 10.1246/cl.150652
  • NAID: 130005108074
  • Peer Reviewed
• [Journal Article] Synthesis of the Polyketide Moiety of the Jamaicamides (2015)
  • Author(s): Ayano Tanaka-Yanuma, Satoshi Watanabe, Keita Ogawa, Sho Watanabe, Naoto Aoki, Tetsuhiro Ogura, Toyonobu Usuki
  • Journal Title: Tetrahedon Letters Volume: 56 Issue: 48 Pages: 6777-6781
  • DOI: 10.1016/j.tetlet.2015.10.069
  • Peer Reviewed
• [Journal Article] Synthesis of Cynaropicrin-d4 (2015)
  • Author(s): Takuya Sato, Shihori Hara, Makiko Sato, Keita Ogawa, Michael Adams, Toyonobu Usuki
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 25 Issue: 23 Pages: 5504-5507
  • DOI: 10.1016/j.bmcl.2015.10.065
  • Peer Reviewed
• [Journal Article] Total Synthesis of the COPD Biomarker Desmosine via Stepwise Sonogashira Cross-Coupling Reactions (2015)
  • Author(s): Haruka Yamada, Takahiro Hayashi, Toyonobu Usuki
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 88 Issue: 5 Pages: 673-683
  • DOI: 10.1246/bcsj.20140394
  • NAID: 130005069507
  • ISSN: 0009-2673, 1348-0634
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Syntheses of Natural and Deuterated Desmosines via Palladium-Catalyzed Cross-Coupling Reactions (2015)
  • Author(s): Rina Suzuki, Hiroto Yanuma, Takahiro Hayashi, Haruka Yamada, Toyonobu Usuki
  • Journal Title: Tetrahedron Volume: 71 Issue: 12 Pages: 1851-1862
  • DOI: 10.1016/j.tet.2015.01.064
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] [13C3,15N1]-Labeled Isodesmosine: a Potential Internal Standard for LC-MS/MS Analysis of Desmosines in Elastin Degradation (2015)
  • Author(s): Takahiro Tanigawa, Akira Komatsu, Toyonobu Usuki
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 25 Issue: 10 Pages: 2046-2049
  • DOI: 10.1016/j.bmcl.2015.03.084
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Pr(OTf)3-promoted Chichibabin Pyridine Synthesis of Isodesmosine in H2O/MeOH (2014)
  • Author(s): Takanori Sugimura, Akira Komatsu, Yohei Koseki, Toyonobu Usuki
  • Journal Title: Tetrahedon Letters Volume: 55 Issue: 46 Pages: 6343-6346
  • DOI: 10.1016/j.tetlet.2014.09.097
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Synthesis and LC-MS/MS Analysis of Desmosine-CH2, a Potential Internal Standard for the Degraded Elastin Biomarker Desmosine (2014)
  • Author(s): Yuko Murakami, Rina Suzuki, Hiroto Yanuma, Jiantao He, Shuren Ma, Gerard M. Turino, Yong Y. Lin, Toyonobu Usuki
  • Journal Title: Organic & Biomolecular Chemistry Volume: 12 Issue: 48 Pages: 9887-9894
  • DOI: 10.1039/c4ob01438c
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Improved Negishi Cross-Coupling Reactions of an Organozinc Reagent Derived from L-Aspartic Acid with Monohalopyridines (2014)
  • Author(s): Toyonobu Usuki, Hiroto Yanuma, Takahiro Hayashi, Haruka Yamada, Noriyuki Suzuki, Yoshiro Masuyama
  • Journal Title: J. Heterocycl. Chem. Volume: 51 Issue: 1 Pages: 269-273
  • DOI: 10.1002/jhet.1807
  • Peer Reviewed
• [Journal Article] Antitrypanosomal Structure-Activity-Relationship Study of Synthetic Cynaropicrin Derivatives (2014)
  • Author(s): Toyonobu Usuki, Makiko Sato, Shihori Hara, Yukiko Yoshimoto, Ryosuke Kondo, Stefanie Zimmermann, Marcel Kaiser, Reto Brun, Matthias Hamburger, Michael Adams
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 24 Issue: 3 Pages: 794-798
  • DOI: 10.1016/j.bmcl.2013.12.099
  • Peer Reviewed
• [Journal Article] Biomimetic Chichibabin Pyridine Synthesis of the COPD Biomarkers and Elastin Crosslinkers Isodesmosine and Desmosine (2014)
  • Author(s): Toyonobu Usuki, Takanori Sugimura, Akira Komatsu, Yohei Koseki
  • Journal Title: Organic Letters Volume: 16 Issue: 6 Pages: 1672-1675
  • DOI: 10.1021/ol500333t
  • Peer Reviewed
• [Journal Article] Structure-Activity Relationship Study of Sesquiterpene Lactones and Their Semi-Synthetic Amino Derivatives as Potential Antitrypanosomal Products (2014)
  • Author(s): Stefanie Zimmermann, Gerda Fouché, Maria De Mieri, Yukiko Yoshimoto, Toyonobu Usuki, Rudzani Nthambeleni, Christopher J. Parkinson, Christiaan van der Westhuyzen, Marcel Kaiser, Matthias Hamburger, Michael Adams
  • Journal Title: Molecules Volume: 19 Issue: 3 Pages: 3523-3538
  • DOI: 10.3390/molecules19033523
  • Peer Reviewed
• [Journal Article] Stable Deuterium Internal Standard for the Isotope-dilution LC-MS/MS Analysis of Elastin Degradation (2013)
  • Author(s): Shuren Ma, Gerard M. Turino, Takahiro Hayashi, Hiroto Yanuma, Toyonobu Usuki, Yong Y. Lin
  • Journal Title: Analytical Biochemistry Volume: 440 Issue: 2 Pages: 158-165
  • DOI: 10.1016/j.ab.2013.05.014
  • Peer Reviewed
• [Journal Article] Improved Synthesis of (R)-7-Hydroxycarvone from (S)-alpha-Pinene (2013)
  • Author(s): Yuki Egoshi, Ryosuke Kondo, Yukiko Yoshimoto, Toru Sugiyama, Toyonobu Usuki
  • Journal Title: Tetrahedron Letters Volume: 54 Issue: 51 Pages: 7029-7030
  • DOI: 10.1016/j.tetlet.2013.10.066
  • Peer Reviewed
• [Presentation] 弾性線維エラスチンの構造解明を目指した環状desmosineの創製 (2016)
  • Author(s): 東海林大、小川圭太、林貴広、臼杵豊展
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学（京都府京田辺市）
  • Year and Date: 2016-03-26
• [Presentation] 同位体標識isodesmosineの合成研究 (2016)
  • Author(s): 田中尚、谷川貴寛、臼杵豊展
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学（京都府京田辺市）
  • Year and Date: 2016-03-26
• [Presentation] Cynaropicrin A環部の合成研究 (2016)
  • Author(s): 内山朋弥、森尊哉、善本由紀子、近藤良佑、臼杵豊展
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学（京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] 植物毒性天然物foeniculoxinの全合成研究 (2016)
  • Author(s): 山岸茜、江越由起、鈴木教之、鈴木由美子、増山芳郎、臼杵豊展
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学（京都府京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] Synthesis of Desmosine-d4 for LC-MS/MS Analysis in Elastin Degradation (2015)
  • Author(s): Daisuke Watanabe, Toyonobu Usuki
  • Organizer: Pacifichem 2015
  • Place of Presentation: Hawaii (USA)
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] [13C3,15N1]-Isodesmosine, a Potential Internal Standard for the LC-MS/MS Analysis in Elastin Degradation (2015)
  • Author(s): Takahiro Tanigawa, Toyonobu Usuki
  • Organizer: Pacifichem 2015
  • Place of Presentation: Hawaii (USA)
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] Synthetic Study of Cnicin (2015)
  • Author(s): Miho Tanigawa, Toyonobu Usuki
  • Organizer: Pacifichem 2015
  • Place of Presentation: Hawaii (USA)
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] Synthetic Study of Cyclic Desmosine for Elucidation of the Crosslinking Structure of Elastin (2015)
  • Author(s): Keita Ogawa, Toyonobu Usuki
  • Organizer: Pacifichem 2015
  • Place of Presentation: Hawaii (USA)
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] Extraction of Flavor Compounds from Lemongrass Utilizing Ionic Liquids (2015)
  • Author(s): Chihiro Murata, Toyonobu Usuki
  • Organizer: Pacifichem 2015
  • Place of Presentation: Hawaii (USA)
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] Extraction of Citral from Lemon Myrtle Utilizing Ionic Liquids (2015)
  • Author(s): Koki Munakata, Toyonobu Usuki
  • Organizer: Pacifichem 2015
  • Place of Presentation: Hawaii (USA)
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] Studies toward the Total Synthesis of Cynaropicrin (2015)
  • Author(s): Takaya Mori, Toyonobu Usuki
  • Organizer: Pacifichem 2015
  • Place of Presentation: Hawaii (USA)
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] エラスチンの三次元架橋構造解明に向けた環状desmosineペプチドの合成研究 (2015)
  • Author(s): 小川圭太、林貴広、臼杵豊展
  • Organizer: 日本化学会第5回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀（東京都江戸川区）
  • Year and Date: 2015-10-13
• [Presentation] レモングラス香気成分のイオン液体抽出法 (2015)
  • Author(s): 村田ちひろ、藤田正博、陸川政弘、臼杵豊展
  • Organizer: 日本化学会第5回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀（東京都江戸川区）
  • Year and Date: 2015-10-13
• [Presentation] 化学合成とイオン液体が拓く超天然物化学 (2015)
  • Author(s): 臼杵豊展
  • Organizer: 岐阜大学大学院応用生物科学研究科 講演会
  • Place of Presentation: 岐阜大学（岐阜県岐阜市）
  • Year and Date: 2015-09-15
  • Invited
• [Presentation] レモンマートル香気成分citralのイオン液体抽出法 (2015)
  • Author(s): 宗像孝紀、藤田正博、陸川政弘、富田祐司、臼杵豊展
  • Organizer: 第59回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 近畿大学（大阪府東大阪市）
  • Year and Date: 2015-09-05
• [Presentation] 抗トリパノソーマ活性天然物cynaropicrinの全合成研究 (2015)
  • Author(s): 森尊哉、善本由紀子、近藤良佑、臼杵豊展
  • Organizer: 第59回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 近畿大学（大阪府東大阪市）
  • Year and Date: 2015-09-05
• [Presentation] Ionic Liquid-Mediated Extraction of Plant Natural Products (2015)
  • Author(s): Toyonobu Usuki, Masahiro Yoshizawa-Fujita
  • Organizer: Inaugural Symposium of the Phytochemical Society of Asia 2015
  • Place of Presentation: 徳島文理大学（徳島県徳島市）
  • Year and Date: 2015-09-01
  • Int'l Joint Research
• [Presentation] イオン液体と天然有機化合物 (2015)
  • Author(s): 臼杵豊展
  • Organizer: 新学術領域研究「天然物ケミカルバイオロジー～分子標的と活性制御」地区ミニシンポジウム
  • Place of Presentation: 東北大学大学院理学研究科（宮城県仙台市）
  • Year and Date: 2015-06-30
  • Invited
• [Presentation] 重水素標識desmosine合成に基づくCOPDバイオマーカーの同位体希釈LC-MS/MS定量分析 (2015)
  • Author(s): 臼杵豊展、鈴木里奈、林貴広、矢沼裕人、山田はるか、馬人、トリーノ・エム・ゲラルド、林栄源
  • Organizer: 日本ケミカルバイオロジー学会 第10回年会
  • Place of Presentation: 東北大学百周年記念会館（宮城県仙台市）
  • Year and Date: 2015-06-11
• [Presentation] 植物毒性天然物foeniculoxinの全合成研究 (2015)
  • Author(s): 江越由起、鈴木教之、鈴木由美子、増山芳郎、臼杵豊展
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-29
• [Presentation] COPDバイオマーカー定量分析を目指した重水素化desmosineの創製 (2015)
  • Author(s): 鈴木里奈、林貴広、矢沼裕人、Yong Y. Lin、臼杵豊展
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-29
• [Presentation] イオン液体による薩摩芋葉有効成分caffeoylquinic acids抽出・単離法の革新 (2015)
  • Author(s): 音田慎吾、藤田正博、陸川政弘、臼杵豊展
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-29
• [Presentation] COPDバイオマーカーisodesmosineのChichibabinピリジン合成 (2015)
  • Author(s): 小松瑛、杉村尚則、谷川貴寛、小関洋平、臼杵豊展
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-27
• [Presentation] Natural Products Research: Organic Synthesis and Ionic Liquids (2014)
  • Author(s): Toyonobu Usuki
  • Organizer: Seminar at the Department of Chemistry, The Chinese University of Hogn Kong
  • Place of Presentation: The Chinese University of Hogn Kong
  • Year and Date: 2014-11-28
  • Invited
• [Presentation] Synthetic Study of Cyclic Desmosine for Elucidation of the Crosslinking Structure of Elastin (2014)
  • Author(s): Keita Ogawa, Takahiro Hayashi, Toyonobu Usuki
  • Organizer: 15th Tetrahedron Symposium - Asian Edition
  • Place of Presentation: Singapore
  • Year and Date: 2014-10-28 – 2014-10-31
• [Presentation] Synthetic Study of Phyllostin, a Potential Mycoherbicide, Produced by Phyllosticta cirsii (2014)
  • Author(s): Takuya Sato, Toyonobu Usuki
  • Organizer: 15th Tetrahedron Symposium - Asian Edition
  • Place of Presentation: Singapore
  • Year and Date: 2014-10-28 – 2014-10-31
• [Presentation] COPDバイオマーカーisodesmosineの全合成 (2014)
  • Author(s): 小松瑛、杉村尚則、谷川貴寛、小関洋平、臼杵豊展
  • Organizer: 日本化学会第4回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀
  • Year and Date: 2014-10-15
• [Presentation] イオン液体による植物由来天然有機化合物の新規獲得法の開発 (2014)
  • Author(s): 音田慎吾、藤田正博、陸川政弘、臼杵豊展
  • Organizer: 第56回天然有機化合物討論会
  • Place of Presentation: 高知県立県民文化ホール
  • Year and Date: 2014-10-15
• [Presentation] イオン液体を利用したレモングラス香気成分の新規抽出法 (2014)
  • Author(s): 村田ちひろ、藤田正博、陸川政弘、臼杵豊展
  • Organizer: 第58回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 和歌山大学
  • Year and Date: 2014-09-20
• [Presentation] 有機合成とイオン液体が拓く超天然物化学 (2014)
  • Author(s): 臼杵豊展
  • Organizer: 新潟薬科大学 講演会
  • Place of Presentation: 新潟薬科大学
  • Year and Date: 2014-07-24
  • Invited
• [Presentation] An Effective Biomarker in Chronic Obstructive Pulmonary Disease (COPD) (2014)
  • Author(s): Shuren Ma, Jiangtao He, Yong Y Lin, Jerome Cantor, Toyonobu Usuki, Gerard Turino
  • Organizer: 62nd ASMS Annual Conference
  • Place of Presentation: Baltimore
  • Year and Date: 2014-06-15 – 2014-06-19
• [Presentation] COPDバイオマーカーisodesmosineのバイオミメティック全合成 (2014)
  • Author(s): 谷川貴寛、小松瑛、杉村尚則、小関洋平、臼杵豊展
  • Organizer: 第67回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 2014-05-17
• [Presentation] 同位体標識とイオン液体による超天然物化学研究 (2014)
  • Author(s): 臼杵豊展
  • Organizer: 第2回慶應有機化学若手シンポジウム
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 2014-05-10
  • Invited
• [Presentation] COPDバイオマーカー診断法の確立：エラスチン架橋分子desmosineのアイソトープ希釈LC-MS/MS法による定量分析 (2014)
  • Author(s): 臼杵豊展、Yong Y. Lin、Gerard M. Turino
  • Organizer: 第54回日本呼吸器学会学術講演会
  • Place of Presentation: 大阪国際会議場
  • Year and Date: 2014-04-27
• [Presentation] Natural Products Research: Chemical Approaches to the Contribution in Medicines (2013)
  • Author(s): Toyonobu Usuki
  • Organizer: Seminar at the Department of Pharmaceutical Sciences, University of Basel
  • Place of Presentation: Basel, Switzerland
  • Invited
• [Presentation] 生物活性天然物のケミカルメディシン研究 (2013)
  • Author(s): 臼杵豊展
  • Organizer: 名古屋大学 Chemistry Seminar
  • Place of Presentation: 名古屋大学
  • Invited
• [Presentation] Bilobalideのイオン液体媒介抽出法の開発 (2013)
  • Author(s): 音田慎吾、藤田正博、陸川政弘、臼杵豊展
  • Organizer: 第57回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 埼玉大学
• [Presentation] 同位体標識desmosineの合成に基づくCOPD（慢性閉塞性肺疾患）バイオマーカー厳密定量法の確立 (2013)
  • Author(s): 鈴木里奈、林貴広、矢沼裕人、Yong Y. Lin、臼杵豊展
  • Organizer: 日本化学会第3回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀
• [Presentation] COPD（慢性閉塞性肺疾患）バイオマーカー定量分析を目指したdesmosine類似体の創製 (2013)
  • Author(s): 村上祐子、矢沼裕人、Yong Y. Lin、臼杵豊展
  • Organizer: 日本化学会第3回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀
• [Presentation] HAT（アフリカ睡眠病）新薬開発へ向けた薬物動態試験用の同位体標識化合物の創製 (2013)
  • Author(s): 佐藤拓哉、原しほり、佐藤麻希子、Michael Adams、臼杵豊展
  • Organizer: 日本化学会第3回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀
• [Presentation] 鈴木－宮浦カップリングによるビアリール型天然有機化合物の合成 (2013)
  • Author(s): 成田修平、小倉徹大、臼杵豊展
  • Organizer: 日本化学会第3回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀
• [Presentation] テルペントリラクトンbilobalideと神経細胞PC-12の構造活性相関 (2013)
  • Author(s): 善本由紀子、佐藤麻希子、竹中妙、吉田雄介、佐竹真幸、鈴木教之、橋爪大輔、臼杵豊展
  • Organizer: 日本化学会第3回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀
• [Presentation] alpha-Pineneから7-hydroxycarvoneの三段階合成 (2013)
  • Author(s): 江越由起、近藤良佑、善本由紀子、杉山徹、臼杵豊展
  • Organizer: 日本化学会第3回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀
• [Presentation] Biomimetic Synthesis of the COPD Biomarker Desmosines (2013)
  • Author(s): Akira Komatsu, Takanori Sugimura, Yohei Koseki, Toyonobu Usuki
  • Organizer: 14th Tetrahedron Symposium - Asian Edition
  • Place of Presentation: Seoul
• [Presentation] Cellulose-dissoluble Ionic Liquid Promotes Extraction and Isolation Efficiency of Natural Products in Ginkgo biloba Leaves (2013)
  • Author(s): Shingo Onda, Nanae Yasuda, Masahiro Yoshizawa-Fujita, Masahiro Rikukawa, Toyonobu Usuki
  • Organizer: 14th Tetrahedron Symposium - Asian Edition
  • Place of Presentation: Seoul
• [Presentation] ケミカルメディシン：COPDバイオマーカー診断法の確立と植物系天然物の革新的獲得法の開発 (2013)
  • Author(s): 臼杵豊展
  • Organizer: 工学院大学 大学院講義
  • Place of Presentation: 工学院大学
  • Invited
• [Remarks] Usuki Research Group - Sophia University
  • URL: http://www.mls.sophia.ac.jp/~usuki/index.html
• [Remarks] 臼杵豊展 准教授 － 教員紹介 － 上智大学 理工学部 物質生命理工学科
  • URL: http://sephiroth.mls.sophia.ac.jp/teacher/archives/000027.html
• [Remarks] 上智大学 理工学部 物質生命理工学科
  • URL: http://rscdb.cc.sophia.ac.jp/Profiles/67/0006622/profile.html
• [Remarks] Usuki Research Group - Sophia Unviersity
  • URL: http://www.mls.sophia.ac.jp/~usuki/index.html
• [Remarks] 臼杵 豊展 准教授 - 教員紹介 - 上智大学 理工学部 物質生命理工学科
  • URL: http://sephiroth.mls.sophia.ac.jp/teacher/archives/000027.html
• [Remarks] 上智大学 理工学部 物質生命理工学科
  • URL: http://rscdb.cc.sophia.ac.jp/Profiles/67/0006622/profile.html
• [Patent(Industrial Property Rights)] カフェオイルキナ酸類抽出方法及びカフェオイルキナ酸類製造方法 (2014)
  • Inventor(s): 臼杵豊展、藤田正博、音田慎吾
  • Industrial Property Rights Holder: 学校法人 上智学院
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2014-092037
  • Filing Date: 2014-04-25
• [Patent(Industrial Property Rights)] COPDバイオマーカーpseudodesmosineの開発 (2014)
  • Inventor(s): 臼杵豊展
  • Industrial Property Rights Holder: 学校法人 上智学院
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2014-055337
  • Filing Date: 2014-03-18
• [Patent(Industrial Property Rights)] デスモシン、イソデスモシン、およびその誘導体の製造方法 (2014)
  • Inventor(s): 臼杵豊展
  • Industrial Property Rights Holder: 学校法人 上智学院
  • Industrial Property Rights Type: 特許
  • Filing Date: 2014-01-24
  • Overseas