Chemistry and biology ofπ-rich molecules

2012 Fiscal Year Final Research Report

• Project Area: Emergence of highly elaborated pai-space and its function
• Project/Area Number: 20108015
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Tohoku University
• Principal Investigator: ISOBE Hiroyuki 東北大学, 大学院・理学研究科, 教授 (30302805)
• Project Period (FY): 2008 – 2012
• Keywords: π豊富分子 / 人工核酸 / 二重らせん / 酵素 / 水銀

Research Abstract

Replacement of intemucleoside phosphodiester linkages ofDNA or RNA with non-natUral structUres would generate intriguing oligonucleotides with fUnctions that could explore the field of medicinal chemistry, chemical biology and materials science. The Nature's choice of phosphine for the intemucleoside linkage is so divine that allows the connection and cleavage of the oligonucleotides at will. We developed non-natUral oligonucleotides with an intenlucleosidic modification. Adopting an effective reaction from the click chemistry, copper-catalyzed Huisgen cycloaddition, we designed and synthesized the new analogues, triazole-linked DNA and RNA(^<TL>DNA/^<TL>RNA). The robust synthesis supported the concise synthesis of oligonucleotides with triazole-linkages and the development of their functions in bioorganic and materials chemistry.

Research Products

• [Journal Article] Molecular bearing of finite carbon nanotube and fullerene in ensemble rolling motion (2013)
  • Author(s): Isobe, H.; Hitosugi, S.; Yamasaki, T.; Iizuka, R
  • Journal Title: Chem. Sci Volume: 4(3) Pages: 1293-1297
  • URL: http://dx.doi.org/10.1039/c3sc22181d
  • Peer Reviewed
• [Journal Article] 磯部寛之,藤野智子 (2012)
  • Author(s): トリアゾール連結核酸の化学
  • Journal Title: 有機合成化学協会誌 Volume: 70 (8) Pages: 821-830
  • Peer Reviewed
• [Journal Article] Hitosugi, S.;Yamasaki, T.; Isobe, H (2012)
  • Author(s): Bottom-up synthesis and thread-in-bead structures of finite (n,0)-zigzag single-wall carbon nanotubes
  • Journal Title: J. Am. Chem. Soc Volume: 134(30) Pages: 12442-12445
  • URL: (http://dx.doi.org/10.1021/ja305723j) Featured in JACS Spotlights (http://dx.doi.org/10.1021/ja3076956)
  • Peer Reviewed
• [Journal Article] Synthesis of triazole-linked analogues of RNA (^<TL>RNA) (2012)
  • Author(s): Fujino, T.; Endo, K.; Yamazaki, N.; Isobe, H
  • Journal Title: Chem. Lett Volume: 41(4) Pages: 403-405
  • URL: http://dx.doi.org/10.1246/cl.2012.403
  • Peer Reviewed
• [Journal Article] Atropisomerism in a belt-persistent nanohoop molecule:Rotational restriction forced by macrocyclic ring strain (2012)
  • Author(s): Hitosugi, S.; Nakanishi, W.; Isobe, H
  • Journal Title: Chem. Asian J Volume: 7(7) Pages: 1550-1552
  • URL: (http://dx.doi.org/10.1002/asia.201200187) Featured in the front cover (http://dx.doi.org/10.1002/asia.201290025)
  • Peer Reviewed
• [Journal Article] Efficient and improved synthesis of triazole-linked DNA (^<TL>DNA)oligomers (2012)
  • Author(s): Fujino, T.; Yamazaki, N.; Hasome, A.; Endo, K.; Isobe, H
  • Journal Title: Tetrahedron Left Volume: 53(7) Pages: 868-870
  • URL: http://dx.doi.org/10.1016/j.tetlet2011.12.026
  • Peer Reviewed
• [Journal Article] Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes (2011)
  • Author(s): Hitosugi, S.; Nakanishi, W.; Yamasaki, T.; Isobe, H
  • Journal Title: Nat. Commun Volume: 2(10) Pages: 5
  • DOI: doi:10.1038/ncomms1505
  • Peer Reviewed
• [Journal Article] Triazole-linked DNA as a primer surrogate in the synthesis of first-strand cDNA (2011)
  • Author(s): Fujino, T.; Yasumoto, K.; Yamazaki, N.; Hasome, A.; Sogawa, K.; Isobe, H
  • Journal Title: Cham Asian J Volume: 7 (11) Pages: 2956-2960
  • URL: http://dx.doi.org/10.1002/asia.201100712
  • Peer Reviewed
• [Journal Article] Illusory molecular expression of"Penrose stairs"by an aromatic hydrocarbon (2011)
  • Author(s): Nakanishi, W.; Matsuno, T.; Ichikawa, J.; Isobe, H
  • Journal Title: Chem. Int. Ed Volume: 50(27) Pages: 6048-6051
  • URL: http://dx.doi.org/10.1002/anie.201102210
  • Peer Reviewed
• [Journal Article] [n] Cyclo-2,7-naphthylenes: Synthesis and isolation of macrocyclic aromatic hydrocarbons having bipolar carrier transport ability (2011)
  • Author(s): Nakanishi, W.; Yoshioka, T.; Taka, H.; Xue, J. Y; Kita, H. Isobe, H
  • Journal Title: Angew. Cham. Int. Ed Volume: 50(23) Pages: 5323-5326
  • URL: http://dx.doi.org/10.1002/anie.201101314
  • Peer Reviewed
• [Journal Article] Electron mobility in a mercury-mediated duplex of triazole-linked DNA(^<TL>DNA) (2011)
  • Author(s): Isobe, H.; Yamazaki, N.; Asano, A.; Fujino, T.; Nakanishi, W.; Seki, S
  • Journal Title: Chem. Lett Volume: 40(3) Pages: 318-319
  • URL: http://dx.doi.org/10.1246/cl.2011.318
  • Peer Reviewed
• [Journal Article] Disilanyl double-pillared bisanthracene: A bipolar carrier transport material for organic light emitting diode devices (2010)
  • Author(s): Nakanishi, W.; Hitosugi, S.; Piskareva, A.; Shimada, Y; Taka, H.; Kita, H.; Isobe, H
  • Journal Title: Angew. Chem. Int. Ed Volume: 49(40) Pages: 7239-7242
  • URL: http://dx.doi.org/10.1002/anie.2010024332
  • Peer Reviewed
• [Journal Article] Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (^<TL>DNA) (2010)
  • Author(s): Fujino, T.; Tsunaka, N.; Guillot-Nieckowski, M.; Nakanishi, W.; Iwamoto, T.; Nakamura, E.; Isobe, H
  • Journal Title: Tetrahedron Lett Volume: 51(15) Pages: 2036-2038
  • URL: http://dx.doi.org/10.1016/j.tetlet.2010.02.046
  • Peer Reviewed
• [Journal Article] Nanometer-size fluorous fullerene vesicles in water and on solid surfaces (2010)
  • Author(s): Homma, T.; Harano, K.; I sobe, H; Nakamura, E
  • Journal Title: Angew. Chem. Int Ed Volume: 49(9) Pages: 1665-1668
  • DOI: 10.1002/anie.200904659
  • Peer Reviewed
• [Journal Article] In vivo gene delivery by cationic tetraamino fullerene (2010)
  • Author(s): Maeda-Mamiya, R.; Noiri, E.; .Isobe, H.; Nakanishi, W.; Okamoto, K.; Doi, K.; Sugaya, T.; Izumi, T.; Homma, T.; Nakamura, E
  • Journal Title: Proc. Natl. Acad. Sci., U.S.A. Volume: 107 (12) Pages: 5339-5344
  • URL: http://dx.doi.org/10.1073/pnas.0909223107
  • Peer Reviewed
• [Journal Article] Convergent synthesis of oligomers of triazole-linked DNA analo gue (^<TL>DNA) in so lution phase (2009)
  • Author(s): Fujino, T.; Yamazaki, N.; Isobe, H
  • Journal Title: Tetrahedron Lett Volume: 50(28) Pages: 4101-4103
  • URL: http://dx.doi.org/10.1016/j.tetlet.2009.04.101
  • Peer Reviewed
• [Presentation] Structural Science of Nanocarbon Molecules: A Synthetic Approach from Organic Chemistry (2013)
  • Author(s): 磯部寛之
  • Organizer: 分子研コロキウム
  • Place of Presentation: 岡崎
  • Year and Date: 2013-01-18
• [Presentation] Molecular design of functional π-systems (2012)
  • Author(s): 磯部寛之
  • Organizer: 岡山理科大学グリーン元素講演会
  • Place of Presentation: 岡山
  • Year and Date: 2012-09-01
• [Presentation] ナノカーボンインスパイアード分子の設計・合成 (2012)
  • Author(s): 磯部寛之
  • Organizer: 第24回 万有札幌シンポジウム
  • Place of Presentation: 札幌
  • Year and Date: 2012-07-07
• [Presentation] π電子豊富分子の科学 (2011)
  • Author(s): 磯部寛之
  • Organizer: 第22回万有仙台シンポジウム
  • Place of Presentation: 仙台
  • Year and Date: 2011-12-19
• [Presentation] Nanocarbon-inspired Molecular Design: Interesting Stairs for Interdisciplinary Research (2011)
  • Author(s): Hiroyuki Isobe
  • Organizer: ISNA-14 (Invited Lecture)
  • Place of Presentation: Oregon, U.S.A.
  • Year and Date: 2011-07-24
• [Presentation] Functional Assembly of Amphiphilic Carbon Clusters (2010)
  • Author(s): Hiroyuki Isobe
  • Organizer: 9th International Symposium on Functionalπ-Electron Systems (Plenary Lecture)
  • Place of Presentation: Georgia, U.S.A.
  • Year and Date: 2010-05-28
• [Presentation] JSPS Asian Core Program (2009)
  • Author(s): Hiroyuki Isobe,
  • Organizer: International Conference on Cutting-Edge Organic Chemistry in Asia Lectureship in Singapore
  • Place of Presentation: Nanyong Technological University, National University of Singapore, Singapore
  • Year and Date: 20091000
• [Presentation] JSPS Asian Core Program (2009)
  • Author(s): Hiroyuki Isobe,
  • Organizer: International Conference on Cutting-Edge Organic Chemistry in Asia LectUreship in China
  • Place of Presentation: Shanhai lnstitute of Organic Chemistry, Shaanxi Normal University, China
  • Year and Date: 20091000
• [Presentation] π電子系を使って見る分子のかたち (2009)
  • Author(s): 磯部寛之
  • Organizer: 第二次先端ウォッチング調査:複合領域の創成,π電子化学-可能性の追求と展望
  • Place of Presentation: 千葉
  • Year and Date: 20090000
• [Presentation] Eye-catching dynamics of small molecules (2009)
  • Author(s): Hiroyuki Isobe
  • Organizer: G-COE Intemational Symposium on Dynamic Phenomena in Molecular Complex Chemistry
  • Place of Presentation: 仙台
  • Year and Date: 2009-10-02
• [Presentation] ナノカーボン有機化学の展開 (2009)
  • Author(s): 磯部寛之
  • Organizer: 基礎有機化学討論会(野副記念奨励賞受賞講演
  • Place of Presentation: 桐生
  • Year and Date: 2009-09-30
• [Presentation] ナノカーボン有機化学から探る組織化機能 (2009)
  • Author(s): 磯部寛之
  • Organizer: 階層横断生命科学シンポジウム
  • Place of Presentation: 和光
  • Year and Date: 2009-08-08
• [Book] 芳香族連結輪状分子シクロアリーレンの科学, 「未来材料を創出するπ電子系の科学:新しい合成・構造・機能化研究(CSJカレントレビュー12)」 (2013)
  • Author(s): 磯部寛之,一杉俊平,中西和嘉
  • Total Pages: 54-60
  • Publisher: 化学同人
• [Book] π電子豊富分子の生体内化学:クリック化学人工核酸, 「高次π空間の創発と機能開発」 (2013)
  • Author(s): 磯部寛之,藤野智子
  • Total Pages: 208-212
  • Publisher: シーエムシー出版
• [Remarks]
  • URL: http://www.orgchem2.chem.tohoku.ac.jp/
• [Patent(Industrial Property Rights)] トリアゾール連結型環状ジヌクレオチド誘導体 (2013)
  • Inventor(s): 磯部寛之,藤野智子,岡田滉大
  • Industrial Property Rights Holder: 東北大学
  • Industrial Property Number: 特許、特願2012-001994
  • Filing Date: 2013-01-09
• [Patent(Industrial Property Rights)] 縮退系大環状分子大環状化合物,ならびに,その結晶および製造方法 (2010)
  • Inventor(s): 磯部寛之,中西和嘉,吉岡知昭
  • Industrial Property Rights Holder: 東北大学
  • Industrial Property Number: 特許、2010-275387
  • Filing Date: 2010-12-10