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(In Japanese)超天然物の反応制御と分子設計

Research report code R000000190
Posted date Sep 30, 2002
Researchers
  • (In Japanese)平間 正博
Affiliation
  • (In Japanese)東北大学大学院理学研究科
Research organization
  • (In Japanese)東北大学大学院理学研究科
Report name (In Japanese)超天然物の反応制御と分子設計
Technology summary (In Japanese)精密化・高速化された有機合成化学を機軸に物理有機化学,コンピュータと分子生物学,構造生物学の進歩を合わせて蛋白質複合体の三次元構造と機能発現の反応原理を解明することを目的としており,原子レベルの反応制御によって天然物の機能を超える次世代の機能性高分子や蛋白質複合系超天然物の合理的分子設計を目指している。主要な研究題目として,
1)1,4-ビラジカル活性種を安定化する蛋白質複合系の原理とデザイン,
2)新しい集積型ポリ-1,4-ビラジカルの設計と反応制御,
3)神経毒ポリエーテルのイオンチャンネル阻害の原理と修復,
4)人工ハプテンによるシガトキシン特異抗体の創出,
5)微量海産生理活性分子,骨そしょう薬ノルゾアンタミンおよび抗癌剤ハロモンの不斉合成法と作用機能
をとりあげた。
Research field
  • Stereochemistry of organic reaction
  • Chemical synthesis
  • Production and application of antigens, antibodies, complements
  • Basic research of antitumor (=antineoplastic) drugs
  • Molecular and genetic information processing
Published papers related (In Japanese)(1)K. Takahashi, M. Hagiwara, S. Ashizawa, and M. Hirama, Concise Synthesis of the Naphthoate Component of N1999-A2. Synlett, 71-72 (1999).
(2)T. Kaneko, M. Takahashi, and M. Hirama, Photochemical Cycloaromatization of Nonbenzenoid Enediynes. Angew. Chem. Internat. Ed. Engl., 38, 1267-1268 (1999).
(3)T. Kaneko, M. Takahashi, and M. Hirama, Benzannelation Alters the Rate Limiting Step in Enediyne Cycloaromatization. Tetrahedron Lett., 40, 2015-2018 (1999).
(4)G. Hirai, H. Oguri, and M. Hirama, Synthetic Study of Zoanthamine Alkaloids: The C-ring Model Possessing Three Consecutive Quaternary Carbons. Chemistry Lett., 141-142 (1999).
(5)K. Kano, H. Kamo, S. Negi, T. Kitae, R. Takaoka, M. Yamaguchi, H. Okubo, and M. Hirama, Chiral recognition of an anionic tetrahelicene by native cyclodextrins. Enantioselectivity dominated by location of a hydrophilic group of the guest in a cyclodextrin cavity. J. Chem. Soc., Perkin Trans. 2, 15-21 (1999).
(6)H. Oguri, S. Sasaki, S. Hishiyama, T. Oishi, M. Hirama, T. Tumuraya, Y. Tomioka, and M. Mizugaki, Designed Hapten Aimed at Anti-ciguatoxin Monocronal Antibody: Synthesis, Immunization and Descrimination of the C2 Configuration. Synthesis, Special Issue, 1431-1436 (1999).
(7)A. Ishiwata, S. Sakamoto, T. Noda, and M. Hirama, Synthetic Study of Pinnatoxin A: Intramolecular Diels-Alder Approach to the AG-ring. Synlett, 692-694 (1999).
(8)A. Nitta, T. Noda, and M. Hirama, Synthetic Study of Pinnatoxin A: Intramolecular Alkylation Approach to the G-ring. Synlett, 695-696 (1999).
(9)I. Sato, T. Kikuchi, and M. Hirama, Synthetic Study of C-1027 Chromophore: Enantioselective Synthesis of b-Tyrosine Moiety and Effective Aryl Ether Formation. Chemistry Lett., 511-512 (1999).
(10)T. Oishi, M. Maruyama, M. Shoji, K. Maeda, N. Kumahara, S. Tanaka, and M. Hirama, Enantioselective Synthesis of the Medium Ring Ethers, Tetrahydrooxepin, Oxocane and Hexahydrooxonin, of Ciguatoxin. Extensive Ring-Expansion and Chemoenzymatic Desymmetrization Strategy. Tetrahedron, 55, 7471-7498 (1999).
(11)K. Maeda, T. Oishi, H. Oguri, and M. Hirama, Convergent Synthesis of the ABCDE Ring Framework of Ciguatoxin. Chem. Commun., 1063-1064 (1999).
(12)M.J. Lear and M. Hirama, Convenient Route to Derivatives of the 2-Deoxysugar Subunits of the Kedarcidin Chromophore: L-Mycarose and L-Kedarosamine. Tetrahedron Lett., 40, 4897-4900 (1999).
(13)H. Uehara, T. Oishi, K. Yoshikawa, K. Machida, and M. Hirama, The Absolute Configuration and Total Synthesis of Korormicin. Tetrahedron Lett., 40, 8641-8644 (1999).
(14)I. Sato, Y. Akahori, T. Sasaki, T. Kikuchi, and M. Hirama, Synthetic Study of C-1027 Chromophore. Highly Stereoselective Glycosylation. Chemistry Lett., 867-868 (1999).
(15)H. Oguri, S. Sasaki, T. Oishi, and M. Hirama, Expeditious Tandem-Metathesis Route to the AB-ring Frament of Ciguatoxin. Tetrahedron Lett., 40, 5405-5408 (1999).
(16)S. Koseki, Y. Fujimura, and M. Hirama, Benzannelation Effect on Enediyne Cycloaromtization: Ab ab Initio Molecular Orbital Study. J. Phys. Chem., 103, 7672-7605 (1999)
(17)F. Yoshimura, S. Kawata, and M. Hirama, Synthetic Study of Kedarcidin Chromophore: Atropselective Construction of the Ansamacrolide. Tetrahedron Lett., 40, 8281-8285 (1999).
(18)T. Oishi, Y. Nagumo, M. Shoji, J.-Y. Le Brazidec, H. Uehara, and M. Hirama, Convergent Synthesis of the IJKLM Ring Fragment of Ciguatoxin CTX3C. Chem. Commun., 2035-2036 (1999).
(19)H. Oguri, S. Tanaka, T. Oishi, and M. Hirama, A Very Short Route to the Functionalized A-ring Moiety of Ciguatoxin. Tetrahedron Lett., 41, 975-978 (2000)
(20)M. Hirama, K. Akiyama, T. Tanaka, T. Noda, K. Iida, I. Sato, R. Hanaishi, S. Fukuda-Ishisaka, M. Ishiguro, T. Otani, and J.E. Leet, Paramagnetic Enediyne Antitumor Antibiotic C-1027: Spin Identification and Characterization of Radical Species. J. Am. Chem. Soc., 122, 720-721 (2000).
Research project
  • Core Research for Evolutional Science and Technology;Single Molecule and Atom Level Reactions
Information research report
  • (In Japanese)平間 正博. 単一分子・原子レベルの反応制御 超天然物の反応制御と分子設計. 戦略的基礎研究推進事業 平成11年度 研究年報.科学技術振興事業団, 2000. p.442 - 444.

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