Development of determination method of absolute configuration of natural products based on induced exciton coupling, computed by quantum chemical calculation

• Project/Area Number: 20590030
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Kyushu University of Health and Welfare
• Principal Investigator: HOSOI Shinzo Kyushu University of Health and Welfare, 薬学部, 准教授 (60209236)
• Co-Investigator(Kenkyū-buntansha): KATSUMOTO Yukiteru 広島大学, 大学院・理学研究科, 助教 (90351741)
• Co-Investigator(Renkei-kenkyūsha): TANAKA Takeyuki 愛媛大学, 学内共同利用施設, 研究員 (50332763)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2008: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
• Keywords: 絶対配置決定 / 円二色性 / 量子化学計算 / 立体配座解析 / カロテノイド / ビナフチル / ステロール / 絶対配置 / 分子力場計算 / 赤外分光

Research Abstract

A straightforward strategy for chiral discrimination in a specified carotenoid, β-isocryptoxanthin using a CD band, which is insensitive to conformational changes, computed by quantum chemical calculation is reported. This protocol may be applicable to estimating the absolute configuration of a number of natural carotenoids.

Research Products

• [Journal Article] Straightforward approach to the discrimination of (4R)- and (4S)-β-isocryptoxanthin from a conformationally insensitive CD band. (2010)
  • Author(s): Shinzo Hosoi, Takeyuki Tanaka, Yukiteru Katsumoto, Takashi Maoka, Toshio Fujiwara, Masayuki Yamashita, Manabu Node
  • Journal Title: Nat.Prod.Commun. 5 Pages: 1733-1736
  • Peer Reviewed
• [Journal Article] Straightforward approach to the discrimination of (4R)- and (4S)-β- isocryptoxanthin from a conformationally insensitive CD band (2010)
  • Author(s): Shinzo Hosoi
  • Journal Title: Natural Product Communications Volume: 5 Pages: 1733-1736
  • Peer Reviewed
• [Journal Article] Effects of dipole interaction and salvation on the C=O stretching band of N,N-dimethylacetamide in nonpolar solutions: Infrared, isotropic and anisotropic Raman measurements. (2009)
  • Author(s): Yukiteru Katsumoto, Takeyuki Tanaka, Yukihiro Ozaki, Shinzo Hosoi
  • Journal Title: Vibrational Spectroscopy 51 Pages: 119-124
  • Peer Reviewed
• [Journal Article] Induced Circular dichroism and conformational analysis of 2,2'-binaphthyl esters derived from primary alcohols possessing a stereogenic center in the β-position. (2009)
  • Author(s): Shinzo Hosoi, Takeyuki Tanaka, Ichiro Takahashi, Akiyo Sakushima, Yukiteru Katsumoto
  • Journal Title: Lett.Org.Chem. 6 Pages: 120-125
  • Peer Reviewed
• [Journal Article] Induced circular dichroism and conformational analysis of 2, 2'-binaphthyl esters derived from primary alcohols possessing a stereogenic center in the β-position (2009)
  • Author(s): Shinzo Hosoi, et al.
  • Journal Title: Letters in Organic Chemistry 6 Pages: 120-125
  • Peer Reviewed
• [Journal Article] Effects of dipole interaction and salvation on the C=0 stretching band of N, N-dimethylacetamide in nonpolar solutions : Infrared, isotropic and anisotropic Raman measurements (2009)
  • Author(s): Yukiteru Katsumoto, et al.
  • Journal Title: Vibrational Spectroscopy (掲載確定)
  • Peer Reviewed
• [Presentation] 誘起円二色性を基盤とするステロール類の3位水酸基の絶対配置決定について (2010)
  • Author(s): 冨士原聡夫、谷口由佳、山下正行、細井信造
  • Organizer: 第60回日本薬学会近畿支部総会・大会
  • Place of Presentation: 大阪
  • Year and Date: 2010-10-30
• [Presentation] 誘起円二色性を基盤とするステロール類の3位水酸基の絶対配置決定について (2010)
  • Author(s): 細井信造
  • Organizer: 第60回日本薬学会近畿支部総会・大会
  • Place of Presentation: 大阪(摂南大学)
  • Year and Date: 2010-10-30
• [Presentation] 誘起円二色性を基盤とするキラルアミン類の絶対配置決定について (2010)
  • Author(s): 冨士原聡夫、谷口由佳、小関稔、山下正行、野出學、細井信造
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-29
• [Presentation] 生理活性化合物の絶対立体化学を決定する新しい方法論の開発研究 (2010)
  • Author(s): 細井信造、冨士原聡夫、谷口由佳、小関稔、野出學
  • Organizer: 難病克服を目指した分子基盤創薬科学の開拓成果発表会
  • Place of Presentation: 京都薬科大学
  • Year and Date: 2010-03-15
• [Presentation] アキラルなビナフチル発色団を有するキラルアミドの誘起円二色性とその絶対配置決定への適用 (2009)
  • Author(s): 冨士原聡夫, 谷口由佳, 小関稔, 細井信造, 野出學
  • Organizer: 第29回有機合成若手セミナー
  • Place of Presentation: 神戸
  • Year and Date: 2009-11-24
• [Presentation] アキラルなビナフチル発色団を有するキラルアミドの誘起円二色性 (2009)
  • Author(s): 谷口由佳, 小関稔, 細井信造, 野出學
  • Organizer: 第59回日本薬学会近畿支部総会・大会
  • Place of Presentation: 大阪
  • Year and Date: 2009-10-24
• [Presentation] (4R)-β-Isocryptoxanthin及びそのベンゾエート体のCDスペクトル:量子化学的アプローチによるカロテノイドの絶対配置推定について (2009)
  • Author(s): 細井信造, 勝本之晶, 田中丈幸, 眞岡孝至, 野出學
  • Organizer: 第51回天然有機化合物討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2009-10-08
• [Presentation] (4R)-β-isocryptoxanthin及びそのベンゾエート体のCDスペクトル:量子化学的アプローチによるカロテノイドの絶対配置推定について (2009)
  • Author(s): 細井信造
  • Organizer: 第51回天然有機化合物討論会
  • Place of Presentation: 名古屋市公会堂
  • Year and Date: 2009-10-08
• [Presentation] (4R)-β-Isocryptoxanthin及びそのベンゾエート体のCDスペクトル:量子化学的アプローチによるカロテノイドの絶対配置推定について (2009)
  • Author(s): 細井信造, 勝本之晶, 田中丈幸, 眞岡孝至, 野出學
  • Organizer: 第23回カロテノイド研究談話会
  • Place of Presentation: 宮城
  • Year and Date: 2009-09-16
• [Presentation] (4R)-β-isocryptoxanthin及びそのベンゾエート体のCDスペクトル:量子化学的アプローチによるカロテノイドの絶対配置推定について (2009)
  • Author(s): 細井信造
  • Organizer: 第23回カロテノイド研究談話会
  • Place of Presentation: 東北大学百周年記念会館川内萩ホール
  • Year and Date: 2009-09-16
• [Presentation] CD study on (4R)-β-isocryptoxanthin and its benzoate: 12th International Conference on Circular Dichroism (2009)
  • Author(s): 細井信造, 勝本之晶, 田中丈幸, 眞岡孝至, 野出學
  • Organizer: 5th Interdisciplinary Symposium on Biological Chirality
  • Place of Presentation: Italy
  • Year and Date: 2009-08-31
• [Presentation] (4R)-β-Isocryptoxanthin及びそのベンゾエート体のCDに関する研究 (2009)
  • Author(s): 細井信造、勝本之晶、田中丈幸、佐久嶋明世、眞岡孝至
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-27
• [Presentation] (4R) -β-Isocryptoxanthinおよびそのベンゾエート体のCDに関する研究 (2009)
  • Author(s): 細井信造, 勝本之晶, 田中丈幸, 佐久嶋明世, 眞岡孝至
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都国際会議場
  • Year and Date: 2009-03-27
• [Presentation] CD Study on(4R)-β-isocryptoxanthin and its benzoate (2009)
  • Author(s): Shinzo Hosoi
  • Organizer: 12^<th>International Conference on Circular Dichroism 5^<th>Interdisciplinary Symposium on Biological Chirality
  • Place of Presentation: Italy(Brescia)