Synthetic Studies on Amide Bond Isosteres and Their Application to Artificial CXCR4 Ligands

• Project/Area Number: 21890113
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Drug development chemistry
• Research Institution: Tokyo Medical and Dental University
• Principal Investigator: NARUMI Tetsuo Tokyo Medical and Dental University, 生体材料工学研究所, 助教 (50547867)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥2,652,000 (Direct Cost: ¥2,040,000、Indirect Cost: ¥612,000); Fiscal Year 2010: ¥1,261,000 (Direct Cost: ¥970,000、Indirect Cost: ¥291,000); Fiscal Year 2009: ¥1,391,000 (Direct Cost: ¥1,070,000、Indirect Cost: ¥321,000)
• Keywords: 医薬品化学 / アミド結合等価体 / ジペプチドイソスター / クロロアルケン / シスアミド等価体 / α,α-ジクロロ-βt-アミノ酸

Research Abstract

Replacement of the planar amide bond with a surrogate alkene substructure represents a promising approach to overcome their major limitations such as poor bioavailability and short physiological half-life, which limit their medicinal and biological use. However, development of effective ground state isosteric and isoelectronic analogues of the amide bond have yet to be developed. In this study, synthetic methodologies for a newly designed chloroalkene dipeptide isosteres (CADIs) were examined to develop diastereoselective, divergent, and practical synthetic approaches toward (Z)-chlororalkene and (E)-chloroalklene isostere skeletons utilizing organocopper-mediated reactions. These studies should contribute to the development of peptidomimetics-based medicinal chemistry.

Research Products

• [Journal Article] Fluorescence-Quenching Screening of Protein Kinase C Ligands with an Environmentally Sensitive Fluorophore (2011)
  • Author(s): W.Nomura, N.Ohashi, Y.Okuda, T.Narumi, T.Ikura, N.Ito, H.Tamamura, 他
  • Journal Title: Bioconjugate Chem. in press
  • Peer Reviewed
• [Journal Article] Synthetic Caged DAG-lactones for Photochemically-controlled Activation of Protein Kinase C (2011)
  • Author(s): W.Nomura, T.Narumi, N.Ohashi, Y.Serizawa, NE.Lewin, PM.Blumberg, T.Furuta, H.Tamamura, 他
  • Journal Title: ChemBioChem 12巻 Pages: 535-539
  • Peer Reviewed
• [Journal Article] Fluorescent-responsive Synthetic C1b Domains of Protein Kinase Cδ as Reporters of Specific High Affinity Ligand Binding (2011)
  • Author(s): N.Ohashi, W.Nomura, T.Narumi, NE.Lewin, K.Itotani, PM.Blumberg, Hirokazu Tamamura, 他
  • Journal Title: Bioconjugate Chem. 22巻 Pages: 82-87
  • Peer Reviewed
• [Journal Article] Azamacrocyclic-metal Complexes as CXCR4 Antagonists (2011)
  • Author(s): T.Tanaka, T.Narumi, T.Ozaki, A.Sohma, N.Ohashi, C.Hashimoto, K.Itotani, W.Nomura, T.Murakami, N.Yamamoto, H.Tamamura, 他
  • Journal Title: ChemMedChem 6巻 Pages: 834-839
  • Peer Reviewed
• [Journal Article] α, α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of a-Peptide a-Ketoacids (2011)
  • Author(s): Narumi T, Bode JW
  • Journal Title: Heterocycles Volume: 82 Pages: 1515-1525
  • Peer Reviewed
• [Journal Article] Fluorescence-Quenching Screening of Protein Kinase C Ligands with an Environmentally Sensitive Fluorophore (2011)
  • Author(s): Nomura W, Narumi T, Ito N, Tamamura H, et al.
  • Journal Title: Bioconjugate Chem Volume: (in press)
  • Peer Reviewed
• [Journal Article] Azamacrocyclic-metal Complexes as CXCR4 Antagonists (2011)
  • Author(s): Tanaka T, Narumi T, Murakami T, Yamamoto N, Tamamura H, et al.
  • Journal Title: Chem Med Chem Volume: (in press)
  • Peer Reviewed
• [Journal Article] Synthetic Caged DAG-lactones for Photochemically-controlled Activation of Protein Kinase C (2011)
  • Author(s): Nomura W, Narumi T, Blumberg PM, Furuta T, Tamamura H, et al.
  • Journal Title: Chem Bio Chem Volume: 12 Pages: 535-539
  • Peer Reviewed
• [Journal Article] Fluorescent-responsive Synthetic C1b Domains of Protein Kinase Cδ as Reporters of Specific High Affinity Ligand Binding (2011)
  • Author(s): Ohashi N, Nomura W, Narumi T, Tamamura H, et al.
  • Journal Title: Bioconjugate Chem Volume: 22 Pages: 82-87
  • Peer Reviewed
• [Journal Article] Bivalent Ligands of CXCR4 with Rigid Linkers for Elucidation of the Dimerization State in Cells (2010)
  • Author(s): T.Tanaka, W.Nomura, T.Narumi, A.Masuda, H.Tamamura, 他
  • Journal Title: J.Am.Chem.Soc. 132巻、45号 Pages: 15899-15901
  • Peer Reviewed
• [Journal Article] α,α-Dichloroisoxazolidinones for the synthesis and chemoselective peptide ligation of α-peptide α-ketoacids (2010)
  • Author(s): T.Narumi, J.W.Bode, 他
  • Journal Title: Heterocycles in press
  • NAID: 10028237739
  • Peer Reviewed
• [Journal Article] CD4 mimics targeting the HIV entry mechanism and their hybrid molecules with a CXCR4 antagonist (2010)
  • Author(s): T.Narumi, C.Ochiai, K.Yoshimura, S.Harada, T.Tanaka, W.Nomura, H.Arai, T.Ozaki, N.Ohashi, S.Matsushita, H.Tamamura, 他
  • Journal Title: Bioorg.Med.Chem.Lett. 20巻 Pages: 5853-5858
  • Peer Reviewed
• [Journal Article] Peptidic HIV integrase inhibitors derived from HIV gene products : structure-activity relationship studies (2010)
  • Author(s): S.Suzuki, K.Maddali, C.Hashimoto, E.Urano, N.Ohashi, T.Tanaka, T.Ozaki, H.Arai, H.Tsutsumi, T.Narumi, W.Nomura, N.Yamamoto, Y.Pommier, JA Komano, H.Tamamura, 他
  • Journal Title: Bioorg.Med.Chem. 18巻 Pages: 6771-6775
  • Peer Reviewed
• [Journal Article] Peptide HIV-1 Integrase Inhibitors from HIV-1 Gene Products (2010)
  • Author(s): S.Suzuki, E.Urano, C.Hashimoto, H.Tsutsumi, T.Nakahara, T.Tanaka, Y.Nakanishi, K.Maddali, Y.Han, M.Hamatake, K.Miyauchi, Y.Pommier, JA.Beutler, W.Sugiura, H.Fuji, T.Hoshino, K.Itotani, W.Nomura, T.Narumi, N.Yamamoto, JA.Komano, H.Tamamura, 他
  • Journal Title: J.Med.Chem. 53巻 Pages: 5356-5360
  • Peer Reviewed
• [Journal Article] Development of crosslink-type tag-probe pairs for fluorescent imaging of proteins (2010)
  • Author(s): W.Nomura, T.Mino, T.Narumi, N.Ohashi, A, Masuda, C.Hashimoto, H.Tsutsumi, H.Tamamura, 他
  • Journal Title: Biopolimers : Peptide Science 94巻 Pages: 843-852
  • Peer Reviewed
• [Journal Article] CD4 mimics targeting the mechanism of HIV entry (2010)
  • Author(s): Y.Yamada, C.Ochiai, K.Yoshimura, T.Tanaka, N.Ohashi, T.Narumi, W.Nomura, S.Harada, S.Matsushita, H.Tamamura
  • Journal Title: Bioorg.Med.Chem.Lett. 20巻 Pages: 354-358
  • Peer Reviewed
• [Journal Article] Remodeling of dynamic structures of HIV-1 envelope proteins leads to synthetic antigen molecules including neutralizing antibodies (2010)
  • Author(s): T.Nakahara, W.Nomura, K.Ohba, A.Ohya, T.Tanak, C.Hashimoto, T.Narumi, T.Murakami, N.Yamamoto, H.Tamamura, 他
  • Journal Title: Bioconjugate Chem. 21巻 Pages: 709-714
  • Peer Reviewed
• [Journal Article] CD4 mimics targeting the mechanism of HIV (2010)
  • Author(s): Yamada Y, Narumi T, Matsushita S, Tamamura H, et al.
  • Journal Title: Bioorg Med Chem Lett Volume: 20 Pages: 354-358
  • Peer Reviewed
• [Journal Article] Remodeling of dynamic structures of HIV-1 envelope proteins leads to synthetic antigen molecules inducing neutralizing antibodies (2010)
  • Author(s): Nakahara T, Nomura W, Narumi T, Yamamoto N, Tamamura H, et al.
  • Journal Title: Bioconjugate Chem Volume: 21(4) Pages: 709-714
  • Peer Reviewed
• [Journal Article] Peptide HIV-1 integrase inhibitors from HIV-1 gene products (2010)
  • Author(s): Suzuki S, Narumi T, Yamamoto N, Tamamura H, etal.
  • Journal Title: J Med Chem Volume: 53(14) Pages: 5356-5360
  • Peer Reviewed
• [Journal Article] Peptidic HIV integrase inhibitors derived from HIV gene products : Structure-activity relationship studies (2010)
  • Author(s): Suzuki S, Yamamoto N, Pommier Y, Narumi T, Tamamura H, et al.
  • Journal Title: Bioorg Med Chem Volume: 18 Pages: 6771-6775
  • Peer Reviewed
• [Journal Article] CD4 mimics targeting the HIV entry mechanism and their hybrid molecules with a CXCR4 antagonist (2010)
  • Author(s): Narumi T, Nomura W, Matsushita S, Tamamura H, et al.
  • Journal Title: Bioorg Med Chem Lett Volume: 20 Pages: 5853-5858
  • Peer Reviewed
• [Journal Article] Bivalent ligands of CXCR4 with rigid linkers for elucidation of dimerization state in cells (2010)
  • Author(s): Tanaka T, Nomura W, NarumiT, Masuda A, Tamamura H
  • Journal Title: J Am Chem Soc Volume: 132(45) Pages: 15899-15901
  • Peer Reviewed
• [Journal Article] Remodeling of Dynamic Structures of HIV-1 Envelope Proteins Leads to Synthetic Antigen Molecules Inducing Neutralizing Antibodies (2010)
  • Author(s): Nakahara T, Nomura W, Ohba K, Ohya A, Tanaka T, Hashimoto C, Narumi T, Murakami T, Yamamoto N, Tamamura H.
  • Journal Title: Bioconjugate Chemistry (in press)
  • Peer Reviewed
• [Journal Article] Synthesis of Biological Evaluation of Selective CXCR4 Antagonists Containing Alkene Dipeptide Isosteres (2010)
  • Author(s): Narumi T, Hayashi R, Tomita K, Kobayashi K, Tanahara N, Ohno H, Naito T, Kodama E, Matsuoka M, Oishi S, Fujii N.
  • Journal Title: Org.Biomol.Chem. 8 Pages: 616-621
  • Peer Reviewed
• [Journal Article] Synthesis and biological evaluation of selective CXCR4 antagonists containing alkene dipeptide isosteres (2009)
  • Author(s): T.Narumi, R.Hayashi, K.Tomita, K.Kobayashi, N.Tanahara, H.Ohno, T.Naito, E.Kodama, M.Matsuoka, S.Oishi, N.Fujii, 他
  • Journal Title: Org.Biomol.Chem. Pages: 616-621
  • Peer Reviewed
• [Journal Article] Synthesis of protein kinase Cδ C1b domain by native chemical ligation methodology and characterization of its folding and ligand binding (2009)
  • Author(s): N.Ohashi, W.Nomura, M.Kato, T.Narumi, N.E.Lewin, P.M.Blumberg, H.Tamamura, 他
  • Journal Title: J.Pep.Sci. 15巻 Pages: 642-646
  • Peer Reviewed
• [Journal Article] Structure-activity relationship study on artificial CXCR4 ligand possessing the cyclic pentapeptide scaffold : the exploration of amino acid residues of pentapeptides by substitutions of several aromatic amino acids (2009)
  • Author(s): T.Tanaka, W.Nomura, T.Narumi, A.Esaka, S.Oishi, N.Ohashi, K.Itotani, B.J.Evans, Z.-X.Wang, S.C.Peiper, N.Fujii, H.Tamamura, 他
  • Journal Title: Org.Biomol.Chem. Pages: 3805-3809
  • Peer Reviewed
• [Journal Article] Peptide Bond Mimicry by (E)-Alkene and (Z)-Fluoroalkene Peptide Isosteres : Synthesis and Bioevaluation of α-Helical Anti-HIV Peptide Analogues (2009)
  • Author(s): S.Oishi, H.Kamitani, Y.Kodera, K.Watanabe, K.Kobayashi, T.Narumi, K.Tomita, H.Ohno, T.Naito, E.Kodama, M.Matsuoka, N.Fujii, 他
  • Journal Title: Org.Biomol.Chem. Pages: 2872-2877
  • Peer Reviewed
• [Journal Article] Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc-Copper-Mediated S_N2' Alkylation (2009)
  • Author(s): K.Kobayashi, T.Narumi, S.Oishi, H.Ohno, N.Fujii, 他
  • Journal Title: J.Org.Chem. 74巻 Pages: 4626-4629
  • Peer Reviewed
• [Journal Article] Synthesis of Fluoroalkene Dipeptide Isosteres by an Intramolecular Redox Reaction Utilizing N-Heterocyclic Carbenes (NHCs) (2009)
  • Author(s): Y.Yamaki, A.Shigenaga, K.Tomita, T.Narumi, N.Fujii, A.Otaka, 他
  • Journal Title: J.Org.Chem. 74巻 Pages: 3272-3277
  • Peer Reviewed
• [Journal Article] Structure-activity relationship study on artificial CXCR4 ligands possessing the cyclic pentapeptide scaffold : the exploration of amino acid residues of pentapeptides by substitutions of several aromatic amino acids (2009)
  • Author(s): Tanaka T, Nomura W, Narumi T, Esaka A, Oishi S, Ohashi N, Itotani K, Evans BJ, Wang Z, Peiper SC, Fujii N, Tamamura H.
  • Journal Title: Org.Biomol.Chem. 7 Pages: 3805-3809
  • Peer Reviewed
• [Journal Article] Synthesis of protein kinase Cδ C1b domain by native chemical ligation methodology and characterization of its folding and ligand binding (2009)
  • Author(s): Ohashi N, Nomura W.Kato M, Narumi T, Lewin NE, Blumberg PM, Tamamura H.
  • Journal Title: J.Pept.Sci. 15(10) Pages: 642-646
  • Peer Reviewed
• [Journal Article] Peptide Bond Mimicry by(E)-Alkene and(Z)-Fluoroalkene Peptide Isosteres : Synthesis and Bioevaluation of α-Helical Anti-HIV Peptide Analogues (2009)
  • Author(s): Oishi S, Kamitani H, Kodera Y, Watanabe K, Kobayashi K, Narumi T, Tomita K, Ohno H, Naito T, Kodama E, Matsuoka M, Fujii N.
  • Journal Title: Org.Biomol.Chem. 14 Pages: 2872-2877
  • Peer Reviewed
• [Journal Article] Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc-Copper-Mediated S_N2' Alkylation (2009)
  • Author(s): Kobayashi K, Narumi T, Oishi S, Ohno H, Fujii N.
  • Journal Title: J.Org.Chem. 74 Pages: 4626-4629
  • Peer Reviewed
• [Journal Article] Synthesis of Fluoroalkene Dipeptide Isosteres by an Intramolecular Redox Reaction Utilizing N-Heterocyclic Carbenes(NHCs) (2009)
  • Author(s): Yamaki Y, Shigenaga A, Tomita K, Narumi T, Fujii N, Otaka A.
  • Journal Title: J.Org.Chem. 74 Pages: 3272-3277
  • Peer Reviewed
• [Presentation] HIV-1外被タンパク質gp120の構造変化誘起を指向した低分子CD4ミミックの創製研究 (2011)
  • Author(s): 鳴海哲夫, 新井啓之、吉村和久、原田恵嘉、野村渉、松下修三、玉村啓和
  • Organizer: 日本薬学会第131年会(震災により中止)
  • Place of Presentation: 静岡
• [Presentation] イミダゾリウム塩の構造最適化を指向した構造活性相関研究 (2011)
  • Author(s): 鳴海哲夫, 玉村啓和
  • Organizer: 日本薬学会第131年会(震災により中止)
  • Place of Presentation: 静岡
• [Presentation] 新規アミド結合等価体クロロアルケン型ジペプチドイソスターの合成研究 (2010)
  • Author(s): 鳴海哲夫, 清家俊輔, 野村渉, 玉村啓和
  • Organizer: 第54回日本薬学会関東支部大会
  • Place of Presentation: 東京
  • Year and Date: 2010-10-02
• [Presentation] HIV外被タンパク質gp120の構造変化誘起を指向した低分子CD4ミミックの創製 (2010)
  • Author(s): 鳴海哲夫, 新井啓之, 落合千裕, 尾崎太郎, 吉村和久, 原田恵嘉, 野村渉, 松下修三, 玉村啓和
  • Organizer: 第54回日本薬学会関東支部大会
  • Place of Presentation: 東京
  • Year and Date: 2010-10-02
• [Presentation] HIV-1マトリックスタンパク質を基にした新規抗HIVペプチドの創出 (2010)
  • Author(s): 小森谷真央, 村上努, 鳴海哲夫, 山本直樹, 玉村啓和, など
  • Organizer: 第54回日本薬学会関東支部大会
  • Place of Presentation: 東京
  • Year and Date: 2010-10-02
• [Presentation] 二核亜鉛錯体型CXCR4アンタゴニストの構造活性相関研究 (2010)
  • Author(s): 尾崎太郎, 田中智博, 鳴海哲夫, 村上努, 玉村啓和, など
  • Organizer: 第54回日本薬学会関東支部大会
  • Place of Presentation: 東京
  • Year and Date: 2010-10-02
• [Presentation] Bode JW. α,α-Dicholoroisoxazolidinones for The Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids. (2010)
  • Author(s): 鳴海哲夫
  • Organizer: 5th International Peptide Symposium.
  • Place of Presentation: Kyoto, Japan
• [Presentation] HIV外被タンパク質gp120の構造変化誘起を指向した低分子CD4ミミックの創製 (2010)
  • Author(s): 鳴海哲夫, 新井啓之, 落合千裕, 尾崎太郎, 吉村和久, 原田恵嘉, 野村渉, 松下修三, 玉村啓和
  • Organizer: 第24回日本エイズ学会学術集会・総会
  • Place of Presentation: 東京
• [Presentation] HIV-1外被タンパク質gp120の構造変化誘起を指向した低分子CD4ミミックの構造活性相関研究 (2010)
  • Author(s): 鳴海哲夫, 新井啓之, 落合千裕, 吉村和久, 原田恵嘉, 野村 渉, 松下修三, 玉村啓和
  • Organizer: 第29回メディシナルケミストリーシンポジウム
  • Place of Presentation: 京都
• [Presentation] HIV侵入の動的超分子機構を模倣した立体構造特異的人工抗原分子の創製 (2010)
  • Author(s): 野村渉, 中原徹, 橋本知恵, 大庭賢二, 相馬晃, 田中智博, 鳴海哲夫, 山本直樹, 玉村啓和
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 愛知
• [Presentation] 有機銅試薬によるクロロアルケン型ジペプチドイソスターの合成研究 (2010)
  • Author(s): 鳴海哲夫, 清家俊輔, 尾崎太郎, 新井啓之, 野村渉, 玉村啓和
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 愛知
• [Presentation] Development of Small CD4 Mimic Molecules that Induce Conformational Changes in gp120. (2010)
  • Author(s): Arai H, Narumi T, Ochiai C, Yoshimura K, Harada S, Tanaka T, Nomura W, Ozaki T, Ohashi N, Matsushita S, Tamamura H
  • Organizer: 11th KUMAMOTO AIDS Seminer・GCOE Joint International Symposium.
  • Place of Presentation: Kumamoto, Japan
• [Presentation] 新規アミド結合等価体の創製研究.クロロアルケン型ジペプチドイソスターの合成研究 (2010)
  • Author(s): 鳴海哲夫, 清家俊輔, 野村渉, 玉村啓和
  • Organizer: 日本ケミカルバイオロジー学会 第5回年会
  • Place of Presentation: 横浜
• [Presentation] HIV-1外被タンパク質gp120の構造変化誘起を指向した低分子CD4ミミックの構造活性相関研究 (2010)
  • Author(s): 鳴海哲夫, 落合千裕, 山田裕子, 吉村和久, 原田恵嘉, 大橋南美, 野村渉, 松下修三, 玉村啓和
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] 新規アミド結合等価体クロロアルケン型ジペプチドイソスターの合成研究 (2010)
  • Author(s): 鳴海哲夫, 清家俊輔, 野村渉, 玉村啓和
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] Elucidation of a Dimerization State of a Chemokine Receptor CXCR4 via Chemical Biology Approach Utilizing Novel Bivalent Ligands with Rigid Polyproline Linkers (2010)
  • Author(s): Tanaka T, Nomura W, Narumi T, Tamamura H
  • Organizer: The 13th Akabori Conference Leipzig 2010:Japanese-German Symposium on Peptide Science
  • Place of Presentation: Leipzig, Germany
• [Presentation] Structure-Activity Relationships of CXCR4 Antagonists Having the Dipicolylamine/Azamacro- Cyclic-Metal Complex Structures (2010)
  • Author(s): Ozaki T, Narumi T, Yamamoto N, Tamamura H, et al.
  • Organizer: 11th KUMAMOTO AIDS Seminer? GCOE Joint International Symposium
  • Place of Presentation: Kumamoto, Japan
• [Presentation] Development of Small CD4 Mimic Molecules that Induce Conformational Changes in gp120 (2010)
  • Author(s): Arai H, Narumi T, Matsushita S, Tamamura H, et al.
  • Organizer: 11th KUMAMOTO AIDS Seminer-GCOEJoint International Symposium
  • Place of Presentation: Kumamoto, Japan
• [Presentation] α, α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids (2010)
  • Author(s): Narumi T, Bode JW
  • Organizer: 5th International Peptide Symposium
  • Place of Presentation: Kyoto, Japan
• [Presentation] Development of a Bivalent Ligand for a Chemokine Receptor CXCR4 by Utilizing Polyproline Helix as a Linker (2010)
  • Author(s): Nomura W, Tanaka T, Masuda A, Narumi T, Tamamura H
  • Organizer: 5th International Peptide Symposium
  • Place of Presentation: Kyoto, Japan
• [Presentation] Synthesis and Evaluation of CXCR4-derived Peptides Targeting the Development of AIDS Vaccines (2010)
  • Author(s): Hashimoto C, Narumi T, Tamamura H, et al.
  • Organizer: 5th International Peptide Symposium
  • Place of Presentation: Kyoto, Japan
• [Presentation] リバースからフォワードヘケミカルゲノミクスを活用した抗HIV剤の創製 (2010)
  • Author(s): 田中智博, 鳴海哲夫、山本直樹, 玉村啓和, など
  • Organizer: 日本ケミカルバイオロジー学会第5回年会
  • Place of Presentation: 横浜
• [Presentation] 堅固なリンカーを有する二価結合型CXCR4リガンドの開発と応用 (2010)
  • Author(s): 田中智博, 野村渉, 鳴海哲夫, 増田朱美, 玉村啓和
  • Organizer: 日本ケミカルバイオロジー学会第5回年会
  • Place of Presentation: 横浜
• [Presentation] HIV-1マトリックスタンパク質を基にした新規抗HIVペプチドの創出 (2010)
  • Author(s): 小森谷真央, 鳴海哲夫、山本直樹, 玉村啓和, など
  • Organizer: 日本ケミカルバイオロジー学会第5回年会
  • Place of Presentation: 横浜
• [Presentation] 2価結合型リガンドの新規デザインによるCXCR4の細胞表面における機能解析 (2010)
  • Author(s): 野村渉, 田中智博, 増田朱美, 鳴海哲夫, 玉村啓和
  • Organizer: 第4回バイオ関連化学シンポジウム
  • Place of Presentation: 大阪
• [Presentation] マトリックスタンパク質を基にした新規抗HWペプチド (2010)
  • Author(s): 小森谷真央, 鳴海哲夫, 山本直樹, 玉村啓和, など
  • Organizer: 第29回メディシナルケミストリーシンポジウム
  • Place of Presentation: 京都
• [Presentation] 細胞膜透過性MA部分ペプチドライブラリーを用いた新規抗HIV-1ペプチドの探索と創出 (2010)
  • Author(s): 村上努, 小森谷真央, 鳴海哲夫, 山本直樹, 玉村啓和, など
  • Organizer: 第58回日本ウイルス学会学術集会
  • Place of Presentation: 徳島
• [Presentation] HIV-1遺伝子産物由来のインテグラーゼ阻害剤の創出 (2010)
  • Author(s): 橋本知恵, 鳴海哲夫, Maddali K、Pommier Y, 山本直樹, 駒野淳, 玉村啓和, など
  • Organizer: 第24回日本エイズ学会学術集会・総会
  • Place of Presentation: 東京
• [Presentation] HIV-1マトリックスタンパク質を基にした新規抗HIVペプチドの創出 (2010)
  • Author(s): 小森谷真央, 鳴海哲夫, 山本直樹, 玉村啓和, など
  • Organizer: 第24回日本エイズ学会学術集会・総会
  • Place of Presentation: 東京
• [Presentation] gp120のCD4結合サイトを模倣した新規抗原分子の創製 (2010)
  • Author(s): 尾崎太郎, 田中智博, 宮内浩典, 鳴海哲夫, 山本直樹, 駒野淳, 玉村啓和, など
  • Organizer: 第24回日本エイズ学会学術集会・総会
  • Place of Presentation: 東京
• [Presentation] 合成抗原ペプチドによるHIV-1 gp41の三量体構造を認識する抗体の誘導 (2010)
  • Author(s): 野村渉, 中原徹, 大矢亜紀, 大庭賢二, 田中智博, 橋本知恵, 鳴海哲夫, 村上努, 山本直樹, 玉村啓和
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] 蛍光を用いたPKCリガンド結合評価法の開発 (2010)
  • Author(s): 大橋南美, 野村渉, 鳴海哲夫, 奥田善章, 伊倉貞吉, 伊藤暢聡, 吉田清嗣, Nancy E.Lewin, Peter M.Blumberg,玉村啓和.
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] エイズワクチンを指向した宿主受容体CXCR4由来抗原分子の創製 (2010)
  • Author(s): 橋本知恵, 野村渉, 田中智博, 中原徹, 鳴海哲夫, 大庭賢二, 村上努, 山本直樹, 玉村啓和
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] 二価型CXCR4リガンドの創製と二量体構造解析への応用 (2010)
  • Author(s): 田中智博, 野村渉, 鳴海哲夫, 玉村啓和
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] ペプチドミメティクを基盤とした阻害剤と新規概念によるワクチン (2009)
  • Author(s): 玉村啓和, 野村渉, 鳴海哲夫, 田中智博, 駒野淳, 山本直樹
  • Organizer: 第82回日本生化学会大会シンポジウム
  • Place of Presentation: 神戸
  • Year and Date: 2009-10-21
• [Presentation] Diastereoselective synthesis of (Z)-fluoroalkene dipeptide isosteres and their incorporation into the selective CXCR4 antagonists. (2009)
  • Author(s): Narumi T, Hayashi R, Tomita K, Kobayashi K, Tanahara N, Ohno H, Naito T, Kodama E, Matsuoka M, Nomura W, Tamamura H, Oishi S, Fujii N.
  • Organizer: The 3rd Asia-Pacific International Peptide Symposium.
  • Place of Presentation: Jeju Island, Korea
• [Presentation] Development of CD4 mimic small molecules targeted for dynamic supramolecular mechanism of HIV entry. (2009)
  • Author(s): Ochiai C, Yoshimura K, Yamada Y, Tanaka T, Narumi T, Nomura W, Shibata J, Hatada M, Matsushita S, Tamamura H
  • Organizer: 第10回熊本エイズセミナー
  • Place of Presentation: 熊本
• [Presentation] Diastereoselcctive synthesis of (Z)-fluoroalkene dipeptide isosteres and their incorporation into the selective CXCR4 antagonists (2009)
  • Author(s): Narumi T, Hayashi R, Tomita K, Kobayashi K, Tanahara N, Ohno H, Naito T, Kodama E, Matsuoka M, Nomura W, Tamamura H, Oishi S, Fujii N.
  • Organizer: The 3rd Asia-Pacific International Peptide Symposium
  • Place of Presentation: Jeju Island, Korea
• [Presentation] Chemical biology approach utilizing novel bivalent ligands for GPCR CXCR4 leads to the elucidation of a dimeric structure (2009)
  • Author(s): Tanaka T, Nomura W, Narumi T, Tamamura H.
  • Organizer: The 3rd Asia-Pacific International Peptide Symposium
  • Place of Presentation: Jeju Island, Korea
• [Presentation] Protein Ligand Biosensors and Fluorescence-based Ligand Screening (2009)
  • Author(s): Nomura W, Narumi T, Ohashi N, Tanaka T, Tamamura H.
  • Organizer: Barcelona BioMed Conferences : Fifth Peptide Engineering Meeting
  • Place of Presentation: Barcelona, Spain
• [Presentation] Study of PKC-dependent cellular signaling in a spatia- and temporal-specific manner by photoactivatable synthetic compounds (2009)
  • Author(s): Nomura W, Serizawa Y, Ohashi N, Okuda Y, Narumi T, Yoshida K, Furuta T, Tamamura H.
  • Organizer: The American Society for Cell Biology 49th Annual Meeting
  • Place of Presentation: San Diego, USA
• [Presentation] キナーゼの細胞内局在機構解明のためのツールとしてのケージド化合物 (2009)
  • Author(s): 野村渉, 芹澤雄樹, 大橋南美, Nancy E.Lewin, 奥田善章, 鳴海哲夫, 吉田清嗣, Peter M.Blumberg, 古田寿昭, 玉村啓和
  • Organizer: 第24回生体機能関連化学シンポジウム,第12回バイオテクノロジー部会シンポジウム
  • Place of Presentation: 福岡
• [Presentation] Development of CD4 mimic small molecules targeted for dynamic supramolecular mechanism of HIV entry (2009)
  • Author(s): Ochiai C, Yoshimura K, Yamada Y, Tanaka T, Narumi T, Nomura W, Shibata J, Hatada M, Matsushita S, Tamamura H.
  • Organizer: 第10回熊本エイズセミナー
  • Place of Presentation: 熊本
• [Presentation] 時間・空間特異的な細胞シグナル解析のためのケージドDAGラクトンの合成 (2009)
  • Author(s): 野村渉, 芹澤雄樹, 大橋南美, 奥田善章, 鳴海哲夫, 吉田清嗣, 古田寿昭, 玉村啓和
  • Organizer: 第46回ペプチド討論会
  • Place of Presentation: 北九州
• [Presentation] リバースからフォワードヘケミカルゲノミクスを基盤とした抗HIV剤の創製 (2009)
  • Author(s): 田中智博, 野村渉, 鳴海哲夫, 吉村和久, 松下修三, 村上努, 駒野淳, 山本直樹, 玉村啓和
  • Organizer: 第46回ペプチド討論会
  • Place of Presentation: 北九州
• [Presentation] HIV外被蛋白質gp41の3量体構造に特異的な抗体を誘導する人工抗原ペプチドの合成 (2009)
  • Author(s): 大矢亜紀, 中原徹, 野村渉, 大庭賢二, 田中智博, 橋本知恵, 鳴海哲夫, 村上努, 山本直樹, 玉村啓和
  • Organizer: 第46回ペプチド討論会
  • Place of Presentation: 北九州
• [Presentation] 蛍光標識を用いたオルソゴナルなPKCリガンド結合活性評価法の開発 (2009)
  • Author(s): 大橋南美, 野村渉, 鳴海哲夫, 奥田善章, 伊倉貞吉, 伊藤暢聡, 吉田清嗣, Lewin NE, Blumberg PM, 玉村啓和
  • Organizer: 第46回ペプチド討論会
  • Place of Presentation: 北九州
• [Presentation] HIV侵入の動的超分子機構を模倣した立体構造制御型人工抗原分子の創製 (2009)
  • Author(s): 中原徹, 野村渉, 大庭賢二, 橋本知恵, 大矢亜紀, 田中智博, 鳴海哲夫, 山本直樹, 玉村啓和
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
• [Presentation] 合成二価型リガンドを用いたCXCR4二量体構造の解析研究 (2009)
  • Author(s): 田中智博, 野村渉, 鳴海哲夫, 玉村啓和
  • Organizer: 第28回メディシナルケミストリーシンポジウム
  • Place of Presentation: 東京
• [Presentation] PKCリガンドの蛍光を用いた洗浄不要型アッセイ法の開発 (2009)
  • Author(s): 奥田善章, 野村渉, 鳴海哲夫, 大橋南美, 玉村啓和
  • Organizer: 第28回メディシナルケミストリーシンポジウム
  • Place of Presentation: 東京
• [Presentation] HIV-1第二受容体CXCR4を基にした合成抗原分子の開発 (2009)
  • Author(s): 橋本知恵, 野村渉, 田中智博, 鳴海哲夫, 大庭賢二, 山本直樹, 玉村啓和
  • Organizer: 第28回メディシナルケミストリーシンポジウム
  • Place of Presentation: 東京
• [Presentation] ペプチドライブラリーを基にしたHIV-1インテグラーゼに対する阻害剤の創製 (2009)
  • Author(s): 中西勇太, 中原徹, 鈴木慎太郎, 田中智博, 大橋南美, 堤浩, 鳴海哲夫, 野村渉, 駒野淳, 山本直樹, 玉村啓和
  • Organizer: 第28回メディシナルケミストリーシンポジウム
  • Place of Presentation: 東京
• [Presentation] HIV-gp41の三量体構造に特異的な中和抗体を誘導する人工抗原ペプチド. (2009)
  • Author(s): 大矢亜紀, 中原徹, 野村渉, 大庭賢二, 田中智博, 橋本知恵, 鳴海哲夫, 村上努, 山本直樹, 玉村啓和
  • Organizer: 第28回メディシナルケミストリーシンポジウム
  • Place of Presentation: 東京
• [Book] ペプチドミメティックによる創薬研究, 生化学特集号「ペプチド科学と生 化学の接点」82巻6号 (2010)
  • Author(s): 鳴海哲夫, 玉村啓和
  • Total Pages: 9
  • Publisher: 日本生化学会 東京
• [Book] From Reverse to Forward Chemical Genomics : Development of Anti-HIV Agent.Peptide Science 2009 (2010)
  • Author(s): Tanaka T, Narumi T, Yamamoto N, Tamamura H, et al.
  • Total Pages: 2
  • Publisher: Kouji Okamoto(Eds.), The Japanese peptide Society, Osaka
• [Book] Peptide Science 2009(Synthesis and Evaluation of Artificial Antigen Peptide Based on theTrimeric Form of HIV Fusion Protein.)(Kouji Okamoto(Eds.)) (2010)
  • Author(s): Ohya A, Nakahara T, Narumi T, Yamamoto N, Tamamura H, et al.
  • Total Pages: 3
  • Publisher: The Japanese peptide Society, Osaka
• [Book] Peptide Science 2009(Caged DAG-Lactones for Study of Cellular Signaling in a Spatial-and Temporal Specific Manner.)(Kouji Okamoto(Eds.)) (2010)
  • Author(s): Nomura W, Narumi T, Furuta T, Tamamura H, et al.
  • Total Pages: 2
  • Publisher: The Japanese peptide Society, Osaka
• [Book] Peptide Science 2009(Fluorescnt-Based Orthogonal Sensing Methods for Double Ealuation inPKC Ligands Screening.)(Kouji Okamoto(Eds.)) (2010)
  • Author(s): Ohashi N, Nomura W, Naurmi T, Blumberg PM, Tamamura H, et al.
  • Total Pages: 2
  • Publisher: The Japanese peptide Society, Osaka
• [Book] Peptide Science 2009 (2010)
  • Author(s): Tanaka T, Nomura W, Narumi T, Yoshimura K, Matsushita S, Murakami T, Komano J, Yamamoto N, Tamamura H.
  • Total Pages: 2
  • Publisher: Kouji Okamoto(Eds.), The Japanese peptide Society, Osaka
• [Book] Peptide Science 2008 (2009)
  • Author(s): Kobayashi K, Narumi T, Oishi S, Ohno H, Fujii N.
  • Total Pages: 2
  • Publisher: Motoyoshi Nomizu(Eds.), The Japanese peptide Society, Osaka
• [Patent(Industrial Property Rights)] ケモカインレセプターCXCR4の二価型アンタゴニストの創製とがん細胞のイメージング方法の開発 (2009)
  • Inventor(s): 玉村啓和、野村渉、鳴海哲夫、田中智博
  • Industrial Property Rights Holder: 玉村啓和、野村渉、鳴海哲夫、田中智博
  • Industrial Property Number: 2009-159771
  • Filing Date: 2009-07-06