Development of artificial peptides reversibly changing their secondary structures in response to reductive condition

• Project/Area Number: 25560226
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Biomedical engineering/Biomaterial science and engineering
• Research Institution: Nagasaki University
• Principal Investigator: OBA Makoto 長崎大学, 医歯薬学総合研究科(薬学系), 准教授 (20396716)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
• Keywords: 機能性ペプチド / 非天然型アミノ酸 / 刺激応答性材料

Outline of Final Research Achievements

I designed seven-membered ring amino acid with disulfide (SS) bond in the side chain and synthesized its-containing peptides. SS bond was cleaved in response to reductive condition, resulting in structural change from cyclic to acyclic side chain. Furthermore, structural change of side chain led to the change in peptide secondary structure of its-containing peptides. We expected that its change would be from helical structure to random structure, however, we could not find such unambiguous change.

Research Products

• [Journal Article] Conformational studies on peptides having dipropylglycine (Dpg) or 1-aminocycloheptanecarboxylic acid (Ac7c) within the sequence of L-leucine (Leu) residues (2016)
  • Author(s): M. Oba, H. Nonaka, M. Doi, M. Tanaka
  • Journal Title: Biopolymers (Pept.Sci.) Volume: 106 Issue: 2 Pages: 210-218
  • DOI: 10.1002/bip.22810
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Protein transfection study using multicellular tumor spheroids of human hepatoma Huh-7 cells (2013)
  • Author(s): Takuma Kato, Masakazu Tanaka, Makoto Oba
  • Journal Title: PLoS ONE Volume: 8 Issue: 12 Pages: e82876-e82876
  • DOI: 10.1371/journal.pone.0082876
  • NAID: 120006986750
  • Peer Reviewed
• [Presentation] Environmentally-responsive cyclic a,a-disubstituted a-amino acids for controlling peptide secondary structures (2015)
  • Author(s): Makoto Oba, Hikaru Nounaka, Kaori Furukawa, Kotomi Toyama, Masakazu Tanaka
  • Organizer: Pacifichem 2015
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] 還元反応に応答して側鎖構造を変化させるジ置換アミノ酸の合成とその含有ペプチドの二次構造解析 (2015)
  • Author(s): 農中ひかる、土井光暢、大庭 誠、田中正一
  • Organizer: 第32回日本薬学会九州支部大会
  • Place of Presentation: 九州保健福祉大学（宮崎県・延岡市）
  • Year and Date: 2015-11-28
• [Presentation] Synthesis of peptides having an a,a-disubstituted amino acid with a variable side chain structure responsive to reduction (2015)
  • Author(s): Hikaru Nonaka, Makoto Oba, Mitsunobu Doi, Masakazu Tanaka
  • Organizer: 第52回ペプチド討論会
  • Place of Presentation: 平塚中央公民館（神奈川県・平塚市）
  • Year and Date: 2015-11-16
• [Presentation] 酸化・還元反応に応答して側鎖構造を変化させるジ置換アミノ酸の合成 (2015)
  • Author(s): 農中ひかる、土井光暢、大庭 誠、田中正一
  • Organizer: 第39回有機電子移動化学討論会
  • Place of Presentation: 長崎大学（長崎県・長崎市）
  • Year and Date: 2015-06-25
• [Presentation] 環境変化に応答して側鎖構造を変化させるジ置換アミノ酸とその含有ペプチドの合成および構造解析 (2015)
  • Author(s): 農中ひかる、土井光暢、大庭 誠、田中正一
  • 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（宮城県・仙台市）
  • Year and Date: 2015-06-10
• [Presentation] 環境変化に応答して側鎖構造を変化させるジ置換アミノ酸とその含有ペプチドの合成 (2015)
  • Author(s): 農中ひかる、土井光暢、大庭 誠、田中正一
  • Organizer: 日本薬学会第135年会
  • Place of Presentation: 神戸 神戸学院大学等
  • Year and Date: 2015-03-25 – 2015-03-28