Solid-phase synthesis in water : devlopment of a method for peptide synthesis with the aim of green chemistry

• Project/Area Number: 17790025
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Kobe Gakuin University
• Principal Investigator: HOJO Keiko Kobe Gakuin University, 薬学部, 助教 (20289028)
• Project Period (FY): 2005 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥3,940,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥240,000); Fiscal Year 2008: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2007: ¥900,000 (Direct Cost: ¥900,000); Fiscal Year 2006: ¥1,000,000 (Direct Cost: ¥1,000,000); Fiscal Year 2005: ¥1,000,000 (Direct Cost: ¥1,000,000)
• Keywords: グリーンサスティナブルケミストリー / 水 / ペプチド合成 / 固相合成 / 水溶性 / 水分散性 / ナノ粒子 / building block / 有機合成 / ペプチド / 縮合反応 / 環境 / ナノテクノロジー / 分散 / 保護アミノ酸 / 水中合成 / 環境対応 / 保護基 / 水溶性保護アミノ酸 / 水中反応

Research Abstract

科学技術における重要課題に「グリーン・サスティブナル ケミストリー」が挙げられ,有機溶媒使用の低減化,毒性の少ない試薬の利用が望まれている.しかし、現在、固相合成のほとんどが有機溶媒中で行われており,水中での試みは特殊な例に限られている。試薬、building block等の水に対する難溶性が、それらを利用した水中反応の試みと一般汎用化を障害している.本研究では、building blockの難溶性解決の方法として水溶性基の導入と水分散性をもたせることを提案し,また,ペプチド合成においてそれを実証した.

Research Products

• [Journal Article] 平成20年度日本ペプチド学会奨励賞を受賞して (2009)
  • Author(s): 北條恵子
  • Journal Title: Peptide News Letter 7 Pages: 3-6
• [Journal Article] Development of the solid-phase peptide synthesis in water (2009)
  • Author(s): Keiko Hojo
  • Journal Title: Peptide Science 2008 45(in press)
  • Peer Reviewed
• [Journal Article] Peptide synthesis in water using Boc-amino acids nanoparticles (2009)
  • Author(s): Keiko Hojo, et.al.
  • Journal Title: PEPTIDE 30(in press)
  • Peer Reviewed
• [Journal Article] development of the aolid-phase peptide synthesis in water (2008)
  • Author(s): Hojo, K
  • Journal Title: Peptide Scienece 2008 Pages: 5-8
  • Peer Reviewed
• [Journal Article] Development of a method for the solid-phase peptide synthesis in water (2008)
  • Author(s): Hojo, K., Ichikawa, H., Fukumori, Y., Kawasaki, K
  • Journal Title: Int. J. pept. Res. Ther 14 Pages: 373-380
  • Peer Reviewed
• [Journal Article] PDevelopment of a method for the solid-phase peptide synthesis in water (2008)
  • Author(s): Keiko Hojo, et.al.
  • Journal Title: Int. J. Pept. Res. Ther 14 Pages: 373-380
  • Peer Reviewed
• [Journal Article] Cell-peneterating peptide as adenovirus vector (2007)
  • Author(s): Kida, S., Maeda, M., Hojo, K., Eto, Y, Mizuguchi, H., Hayakawa, T., Mayumi, T., Nakagawa, S., Kawasaki, K
  • Journal Title: Peptide Science Pages: 337-340
  • Peer Reviewed
• [Journal Article] Preoaration of a Tat related transporter peptide for carrying the adenovirus vector into cells (2007)
  • Author(s): Kida, S., Maeda, M., Hojo, K., Eto, Y, Mizuguchi, H., Hayakawa, T., Mayumi, T., Nakagawa, S., Kawasaki, K
  • Journal Title: Protein & Peptide Letters 15 Pages: 219-222
  • Peer Reviewed
• [Journal Article] Solid-phase peptide synthesis using amino acid nanoparticles in water (2007)
  • Author(s): Hojo, K., Ichikawa, H., Maeda, M., Kida, S., Fukumori, Y., Kawasaki, K
  • Journal Title: PEPTIDES 29 Pages: 108-109
  • Peer Reviewed
• [Journal Article] (2007)
  • Author(s): Kida, S., Maeda, M., Hojo, K., Eto, Y, Nakagawa, S., Kawasaki, K
  • Journal Title: Chem Pharm Bull 55 Pages: 685-687
  • Peer Reviewed
• [Journal Article] Solid-phase peptide synthesis using nanoparticulate amino acids in water (2007)
  • Author(s): Hojo, K., et. al.
  • Journal Title: J. Peptide. Res. 13 Pages: 493-497
  • Peer Reviewed
• [Journal Article] Solid-phase peptide syntesis using nanoparticulate Fmoc-amino acid In water (2007)
  • Author(s): Hojo, K., et. al.
  • Journal Title: Peptides 2006 2006 Pages: 108-109
  • Peer Reviewed
• [Journal Article] Studies on Heterobifunctional Cross-Linking Reagents, 6-Maleimidohexanoic Acid Acitive Esters. (2007)
  • Author(s): Kida, S, Hojo, K., et. al.
  • Journal Title: Chem. Pharm. Bull. 55 Pages: 658-687
  • Peer Reviewed
• [Journal Article] An automated peptide and protein thiazolidine coupling chemistry for biosensor immobilization giving a unique N-terminal orientation. (2007)
  • Author(s): Wade, J.D., Hojo, K., Kawasaki, K., Johns, T.G, Catimel B., Rothacker, J., Nice, E.C.
  • Journal Title: Anal. Biochem. 348・8 Pages: 315-317
• [Journal Article] Synthesis of a RGD peptide-PEG hybrid for carrying adenovirus vector into cells. (2007)
  • Author(s): Kida, S., Maeda, M., Hojo, K., Eto, Y., Gao, J.Q., Kurachi, S., Sekiguchi, F., Mizuguchi, H., Hayakawa, T., Mayumi, T., Nakagawa, S., Kawasaki, K.
  • Journal Title: Understanding Biology Using Peptides Pages: 497-498
• [Journal Article] peptide synthesis in water. 2-(4-sulfophenylsulfonyl)ethoxycarbonyl group and coupling reagents (2006)
  • Author(s): Hojo, K., Maeda, M., Kawasaki, K
  • Journal Title: Understnading Biology Using Peptides Pages: 74-75
  • Peer Reviewed
• [Journal Article] Synthesis of a RGD peptide-PEG hybrid for carrying adenovirus vector into cells (2006)
  • Author(s): Kida, S., Maeda, M., Hojo, K., Eto, Y, Mizuguchi, H., Hayakawa, T., Mayumi, T., Nakagawa, S., Kawasaki, K
  • Journal Title: Understnading Biology Using Peptides Pages: 497-498
  • Peer Reviewed
• [Journal Article] Solid phase synthesis in waterVI: evaluation of water-soluble coupling reagents for solid phase peptide synthesis in aqueous media (2006)
  • Author(s): Hojo, K., Maeda, M., Tanakamaru, N., Mochida, K., Kawasaki, K
  • Journal Title: Protein Pept. Lett 13 Pages: 189-92
  • Peer Reviewed
• [Journal Article] Design and synthesis of a Tat-related gene transporter: atool foe carrying the adenovirus vector into cells (2006)
  • Author(s): Kida, S., Maeda, M., Hojo, K., Eto, Y., Gao, JO., Kurachi, S., Mizuguchi, H., Hayakawa, T., Mayumi, T., Nakagawa, S., Kawasaki, K
  • Journal Title: Bioorg. Med. Chem. Lett 16 Pages: 743-745
  • Peer Reviewed
• [Journal Article] Solid-phase synthesis in water using nanoparticulate Fmoc-amino acids (2006)
  • Author(s): Hojo, K., Ichikawa, H., Kida, S., Maeda, M., Fukumori, Y., Kawasaki, K
  • Journal Title: Peptide Science 2006 Pages: 56-56
  • Peer Reviewed
• [Journal Article] An automated peptide and protein thiazolidine coupling chemistry for biosensor immobilization biving a unique N-termial orientation (2006)
  • Author(s): Wade, J.D., Hojo. K., Kawasaki, K., Johns, T.G., Gatimel B., Rothacker, J., Nice, E.C
  • Journal Title: Anal Biochem 348 Pages: 315-317
  • Peer Reviewed
• [Journal Article] Synthesis of peptide mimetics that related to thrombin receptor and their agonist/antagonist acitivities and platelet aggregation (2006)
  • Author(s): Maeda, M., Ueda, K., Hojo, K
  • Journal Title: Peptide Science 2005 Pages: 447-448
  • Peer Reviewed
• [Journal Article] Solid phase peptide synthesis in water VI : evaluation of water-soluble coupling reagents for solid phase peptide synthesis in aqueous media. (2006)
  • Author(s): Hojo, K., Maeda, M., Tanakamaru, N., Mochida, K., Kawasaki, K.
  • Journal Title: Protein Pept. Lett. 13・2 Pages: 189-192
• [Journal Article] Design and synthesis of a Tat-related gene transporter : a tool for carrying the adenovirus vector into cells. (2006)
  • Author(s): Kida, S., Maeda, M., Hojo, K., Eto, Y., Gao, J.Q., Kurachi, S., Mizuguchi, H., Hayakawa, T., Mayumi, T., Nakagawa, S., Kawasaki, K.
  • Journal Title: Bioorg. Med. Chem. Lett. 16・3 Pages: 743-745
• [Journal Article] Synthesis of peptide mimetics that related to tethered thrombin receptor and their agonist/antagonist activities on platelet aggregation (2006)
  • Author(s): Maeda, M, Ueda, K., Hojo, K., Kawasaki, K.
  • Journal Title: Peptide Science 2005 Pages: 447-448
• [Journal Article] "Solid phase synthesis in water" using Fmoc-amino acid nanoparticles. (2006)
  • Author(s): Hojo, K., Ichikawa, H., Maeda, M., Kida, S., Fukumori, Y., Kawasaki, K.
  • Journal Title: Peptide Science 2006 Pages: 56-56
• [Journal Article] A new water-soluble protecting group, 2,4-sulfophenylsulfonyl)ethoxycarbonyl group, and its application to solid-phase peptide synthesis in water (2005)
  • Author(s): Hojo, K., Maeda, M., Kawasaki, K
  • Journal Title: PEPTIDES 28 Pages: 339-340
• [Presentation] Boc保護アミノ酸ナノ粒子を用いる水中ペプチド合成(その2) (2009)
  • Author(s): 北條恵子, その他
  • Organizer: 第129年会
  • Place of Presentation: 京都国際会議場, 京都
  • Year and Date: 2009-03-27
• [Presentation] Development of a method for the solid-phase peptide synthesis in water (2008)
  • Author(s): 北條恵子(招待講演)
  • Organizer: 関西冬のペプチドセミナー
  • Place of Presentation: 大阪
  • Year and Date: 2008-12-06
• [Presentation] Development of a method for solid phase peptide synthesis in water (2008)
  • Author(s): Keiko Hojo
  • Organizer: 関西冬のペプチドセミナー
  • Place of Presentation: 近畿大学, 大阪
  • Year and Date: 2008-12-06
• [Presentation] Development of the solid phase peptide synthesis in water (2008)
  • Author(s): Keiko Hojo
  • Organizer: 第45回ペプチド討論会
  • Place of Presentation: 船橋タワーホール, 東京
  • Year and Date: 2008-10-30
• [Presentation] 水分散型Boc保護アミノ酸ナノ粒子を用いた水中合成 (2008)
  • Author(s): 北條恵子,市川秀喜,福森義信,川崎紘一
  • Organizer: 第58回日本薬学会近畿支部総会・大会
  • Place of Presentation: 神戸薬科大学
  • Year and Date: 2008-10-25
• [Presentation] Boc保護アミノ酸ナノ粒子を用いる水中ペプチド合成 (2008)
  • Author(s): 北條恵子, その他
  • Organizer: 第58回日本薬学会近畿支部総会大会
  • Place of Presentation: 神戸薬科大学, 神戸
  • Year and Date: 2008-10-23
• [Presentation] Development of the solid-phase peptide synthesis in water (2008)
  • Author(s): Keiko Hojo(日本ペプチド学会奨励賞受賞講演)
  • Organizer: 第45回ペプチド討論会
  • Place of Presentation: 東京
• [Presentation] Peptide synthesis in water using Boc-amino acid nanoparticles (2008)
  • Author(s): Hojo, K., Ichikawa, H., Maeda, Fukumori, Y., Kawasaki, K
  • Organizer: 30th European Peptide Symposium
  • Place of Presentation: Helsinki, Finland
• [Presentation] 水分散型保護アミノ酸ナノ粒子を用いた水中固相合成(その2) (2008)
  • Author(s): 北條恵子,市川秀喜,前田光子,喜田進也,福森義信,川崎紘一
  • Organizer: 第128回日本薬学会年会
  • Place of Presentation: 横浜
• [Presentation] Peptide synthesis in water using Boc-amino acid nanoparticles (2008)
  • Author(s): Keiko Hojo, et.al.
  • Organizer: 30^<th> European Peptide Symposium
  • Place of Presentation: ヘルシンキ, フィンランド
• [Presentation] Solid-phase Peptide Synthesis in water : Application of Amino Acids Nanoparticles (2007)
  • Author(s): 北條恵子,市川秀喜,前田光子,喜田進也,福森義信,川崎紘一
  • Organizer: 関西冬のペプチドセミナー
  • Place of Presentation: 大阪
  • Year and Date: 2007-12-08
• [Presentation] Development of the solid-phase peptide synthesis in water (2007)
  • Author(s): 北條恵子、その他
  • Organizer: 関西冬のペプチドセミナー
  • Place of Presentation: 大阪
  • Year and Date: 2007-12-08
• [Presentation] 粉砕技術をもっと利用しよう (2007)
  • Author(s): 市川秀喜,北條恵子,川崎紘一,福森義信
  • Organizer: APPIE産学官連携フェア2007
  • Place of Presentation: 大阪
  • Year and Date: 2007-10-18
• [Presentation] Adenovirus Vector Carrierとしての細胞膜透過ペプチド (2007)
  • Author(s): 喜田進也,衛藤佑介,Ratima Asavatanabodee,前田光子,吉岡靖雄,中川晋作,北條恵子,津田裕子,真弓忠範,川崎紘一
  • Organizer: 第44回ペプチド討論会
  • Place of Presentation: 富山
• [Presentation] Development of Solid-Phase Peptide Synthesis in Water (2007)
  • Author(s): Hojo, K., Ichikawa, H., Maeda, M., Kida, S., Fukumori, Y., Kawasaki, K
  • Organizer: Modern Solid Phase Peptide Synthesis & Its Application
  • Place of Presentation: Port Douglas, Australia
• [Presentation] Adenovirus Vector Carrierとしての細胞膜透過ペプチド (2007)
  • Author(s): 喜田進也,前田光子,北條恵子,衛藤佑介,森重智弘,渡邊光,Ratima Asavatanabodee,吉岡靖雄,水口裕之,真弓忠範,中川晋作,川崎紘一
  • Organizer: 第127回日本薬学会年会
  • Place of Presentation: 富山
• [Presentation] 水分散型Fmoc保護アミノ酸ナノ粒子を用いた水中固相合成法の開発 (2007)
  • Author(s): 北條恵子,市川秀喜,前田光子,喜田進也,福森義信,川崎紘一
  • Organizer: 第127回日本薬学会年会
  • Place of Presentation: 富山
• [Presentation] Adenovirus Vector Carrierとしての細胞膜透過ペプチド (2007)
  • Author(s): 喜田進也,前田光子,北條恵子,衛藤佑介,森重智弘,渡辺光,Ratima Asavatanabodee,吉岡靖雄,水口裕之,眞弓忠範、中川晋作,川崎紘一
  • Organizer: 第127年会日本薬学会
  • Place of Presentation: 富山
• [Presentation] 水分散型Fmoc保護アミノ酸ナノ粒子を用いた水中固相合成法の開発 (2007)
  • Author(s): 北條恵子, 市川秀喜, 前田光子, 喜田進也, 福森義信, 川崎紘一
  • Organizer: 第127年会日本薬学会
  • Place of Presentation: 富山
• [Presentation] Adenovirus Vector carrierとしての細胞膜透過ペプチド (2007)
  • Author(s): 喜田進也、北條恵子、その他
  • Organizer: 日本薬学会第127回年会
  • Place of Presentation: 富山
• [Presentation] 水分散型Fmoc保護アミノ酸ナノ粒子を用いた水中固相合成法の開発 (2007)
  • Author(s): 北條恵子、その他
  • Organizer: 日本薬学会第127回年会
  • Place of Presentation: 富山
• [Presentation] Solid-phase peptide synthesis in water using amino-acid nanoparticles (2007)
  • Author(s): Hojo, K., et. al.
  • Organizer: 9th International Symposium, Solid Phase Synthesis
  • Place of Presentation: Norwich, UK
• [Presentation] DeveloPment of the solid-phase peptide synthesis in water (2007)
  • Author(s): Hojo, K., et. al.
  • Organizer: Modern Solid Phase Peptide Synthesis& Its Application
  • Place of Presentation: Port Douglas, Australia
• [Presentation] Design and synthesis of a Tat-related gene transporter: a tool for carrying the adenovirus vector into cells (2007)
  • Author(s): Kida, S, Hojo, K., et. al.
  • Organizer: 7th International Australian Peptide Sympsium
  • Place of Presentation: Cairns, Australia
• [Presentation] 水分散型Fmoc保護アミノ酸ナノ粒子を用いた水中固相合成法の開発(その2) (2007)
  • Author(s): 北條恵子、その他
  • Organizer: 日本薬学会第128回年会
  • Place of Presentation: 横浜
• [Presentation] 効率的な遺伝子細胞内送達のためのアデノウイルスベクター修飾用細胞膜透過性キャリアーペプチドの合成 (2007)
  • Author(s): 喜田進也、北條恵子、その他
  • Organizer: 日本薬学会第128回年会
  • Place of Presentation: 横浜
• [Presentation] Solid Phase Synthesis in Water Using Fmoc-Amino Acid Nanoparticles (2006)
  • Author(s): 北條恵子, 市川秀喜, 前田光子, 喜田進也, 福森義信, 川崎紘一
  • Organizer: 第43回ペプチド討論会・第4回ペプチド工学国際会議
  • Place of Presentation: 横浜
• [Presentation] Solid Phase Synthesis in Water Using Nanoparticulate Amino Acids (2006)
  • Author(s): 北條恵子, 市川秀喜, 前田光子, 喜田進也, 福森義信, 川崎紘一
  • Organizer: 第29回 European Peptide Symposium
  • Place of Presentation: Gdansk, Poland
• [Presentation] 水中固相合成〜Sps基を用いる完全水系でのDermorphinの合成 (2005)
  • Author(s): 北條恵子,市川裕佳,原田慎一,前田光子,川崎紘一
  • Organizer: 第55回日本薬学会近畿支部大会
  • Place of Presentation: 武庫川女子大
  • Year and Date: 2005-10-29
• [Presentation] アデノウイルスベクター用細胞内移行性ペプチドの合成 (2005)
  • Author(s): 喜田進也,前田光子,北條恵子,衛藤佑介,高建青,倉知慎之輔,森重智弘,水口裕之,真弓忠範、中川晋作、川崎紘一
  • Organizer: 第55回日本薬学会近畿支部大会
  • Place of Presentation: 武庫川女子大
  • Year and Date: 2005-10-29
• [Presentation] Design and Synthesis of a Tat-related Gene Transporter: A Tool for Carrying the Adenovirus Vector into Cells (2005)
  • Author(s): 喜田進也,前田光子,北條恵子,衛藤佑介,高建青,倉知慎之輔,水口裕行,早川堯夫,真弓忠範,中川晋作,川崎紘一
  • Organizer: 第6回Australian Peptide Conference Symposium
  • Place of Presentation: Great Barrier Reef , Australia
• [Presentation] トロンビン受容体関連ペプチドの合成とその活性について (2005)
  • Author(s): 前田光子,上田香織,北條恵子,川崎紘一
  • Organizer: 第42回ペプチド討論会
  • Place of Presentation: 大阪
• [Presentation] Peptide synthesis in water: application of Boc-amino acid nanoparticles
  • Author(s): 北條恵子,市川秀喜,福森義信,川崎紘一
  • Organizer: 関西冬のペプチドセミナー
  • Place of Presentation: 大阪
• [Patent(Industrial Property Rights)] ペプチド合成方法及び該方法に使用可能な水性分散液 (2006)
  • Inventor(s): 菅原(北條)恵子,市川秀喜,福森義信,川崎紘一,金子貫太郎,吉川隆輔
  • Industrial Property Rights Holder: 菅原(北條)恵子,市川秀喜,株式会社栗本鐵工所
  • Industrial Property Number: 2006-232837
  • Filing Date: 2006-08-02
• [Patent(Industrial Property Rights)] ペプチド合成方法及び該方法に使用可能な小性分散液 (2006)
  • Inventor(s): 菅原(北條)恵子, 市川秀喜, 福森義信, 川崎紘一, 金子貫太郎, 吉川隆輔
  • Industrial Property Rights Holder: 菅原(北條)恵子, 市川秀喜, 福森義信, 川崎紘一, 金子貫太郎, 吉川隆輔
  • Industrial Property Number: 2006-232837
  • Filing Date: 2006-09-01