Kyushu University Academic Staff Educational and Research Activities Database
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Hiroshi Suemune Last modified date:2015.9.30

Graduate School
Undergraduate School

Home page of synthetic organic chemistry lab.
Contents: research activities, list of papers and members..
Academic Degree
Ph. D
Field of Specialization
Pharmaceutical Synthetic Chemistry
Outline Activities
Outline of research: Synthetic studies of poly-peptide and nucleic acids with novel functionality.
Outline of education: Organic chemistry for graduate students is open. Organic chemistry III for undergraduate students is open.
Research Interests
  • Study of helicene molecule with high functions
    keyword : helicene, helical chirality, azuleno-helicene
  • Design of Organic Molecular Catalyst
    keyword : Organic Molecular Catalyst, process chemistry, control of reaction
  • Molecular design of novel nucleic acids
    keyword : spin rabeling, nucleoside, ESR, nucleotide
  • Control of herical structure of peptide using novel amino acids
    keyword : amino acid, peptide, herical structure
Academic Activities
1. Hiroshi Suemune, Kazuteru Usui, Kosuke Yamamoto, Kensuke Tanoue, Takashi Shimizu,Synthesis of Substituted Azulenes via Pt(II)-Catalyzed Ring Expanding Cycloisomerization,Org. Lett,2014.08.
2. Makoto Oba, Hiroshi Suemune, Masakazu Tanaka, Naoko Ishikawa,Helical Oligomers with a Changeable Chiral Acetal Moiety,Eur. J. Org. Chem.,Vol.15,pp.7679-7682,2013.11.
3. Hiroshi Suemune, Kazuteru Usui, Kosuke Yamamoto, Mieko Okazumi,Synthesis of [5]Helicenes with a Substituent Exclusively on the Interior Side of the Helix by Metal-catalyzed Cycloisomerization,Org. Lett,Vol.15,pp.1806-1809,2013.03.
4. Yang, B., Jinnouchi, A., Suemune, H., Aso, M. ,Difluoro-C4'-oxidized abasic site for efficient amine modification in biological systems,Org. Lett,Vol.14,No.23,pp.5852-5855,2012.11.
5. Kogiso, T., Yamamoto, K., Suemune, H., Usui, K. ,Synthesis and characterization of 1,8-naphthalimide with [6]helicene skeleton,Org. Biomol. Chem.,10, 2934-2936
6. Demizu, Y., Doi, M., Kurihara, M., Maruyama, T., Suemune, H., Tanaka, M.,One-Handed Helical Screw Direction of Homopeptide Foldamer Exclusively Induced by Cyclic α-Amino Acid Side-Chain Chiral Centers , Chemistry-A European Journal ,18(8), 2430-2439,2012.03.
7. Yosuke Demizu, Mitsunobu Doi, Masaaki Kurihara, Haruhiro Okuda, Masanobu Nagano, Hiroshi Suemune and Masakazu Tanaka,Conformational studies on peptides containing a,a-disubstituted a-amino acids: chiral cyclic a,a-disubstituted a-amino acid as an a-helical inducer,Org. Biomol. Chem.,9, 3303-3312,2011.09.
8. Yuji Nakamura, Yasuyuki Ogawa, Chie Suzuki, Teppei Fujimoto, Shojiro Miyazaki, Kazuhiko Tamaki, Takahide Nishi, and Hiroshi Suemune,EFFICIENT SYNTHESIS OF 5-AMINO-6-DIALKYLAMINO-4-HYDROXYPENTANAMIDE DERIVATIVES FOR RENIN INHIBITORS,Heterocycles,83 (7), 1587-1602,2011.07.
9. Nagano, M., Doi, M., Kurihara, M., Suemune, H., Tanaka, M,Stabilized α-Helix-Catalyzed Enantioselective Epoxidation of α,β-Unsaturated Ketones, Organic Letters,12(15), 3564-3566,2010.11.
10. Demizu, Y., Tanaka, M., Doi, M., Kurihara, M., Okuda, H., Suemune, H,Conformations of peptides containing a chiral cyclic α,α-disubstituted α-amino acid within the sequence of Aib residues,Journal of Peptide Science,16(11), 621-626,2010.10.
11. Nagano, M., Tnaka, M., Doi, M., Demizu, Y., Kurihara, M., Suemune, H.
,Helical-Screw Directions of Diastereoisomeric Cyclic α-Amino Acid Oligomers ,Organic Letters,11 (5), 1135-1137,2009.10.
12. Usui, K., Aso, M., Fukuda, M., Suemune, H.,Photochemical Generation of Oligodeoxynucleotide Containing a C4’-Oxidized Abasic Site and Its Efficient Amine Modification: Dependence on Structure and Microenvironment,J. Org. Chem,73, 241-248(2008),2008.04.
13. M. Imai, M. Tanaka, S. Nagumo, N. Kawahara , and H. Suemune,Nitrile-Promoted Rh-Catalyzed Intermolecular Hydroacylation of Olefins with Salicylaldehyde,J. Org. Chem.,72 (7), 2543-2546,2007.04.
14. M. Aso, K. Usui, M. Fukuda, Y. Kakihara, T. Goromaru, H. Suemune, ,Photochemical Generation of C4'-Oxidized Abasic Site Containing Oligodeoxynucleotide and Its Efficient Amine Modification,Org. Lett.,8(15),3183-3186 ,2006.04.
15. M. Tanaka, M. Kurihara, M. Doi,Side-chain chiral center of amino acid and herical-screw handedness of its peptide,J. Am. Chem. Soc.,Vol.127,No.33,127 (33), 11570-11571,2005.09.
16. K. Tanaka, M. Tanaka, and H. Suemune,Rh-catalyzed p-facial selective intermolecular hydroacylation of norbornenes
,Tetrahedron Letters,Vol.46,No.36,46(36),6053-6056,2005.08.
17. M. Oba, M. Tanaka, Y. Takano, H. Suemune,Concise synthetic strategy toward cyclic alpha,alpha-disubstituted alpha-amino acids bearing a delta-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids,Tetrahedron,Vol.61,No.3,61, 593-598,2005.03.
18. T. Kaneko, M. Aso, N. Koga, and H. Suemune,Synthesis and EPR Studies of 2-N-tert-Butylaminoxylpurine Derivatives,Org. Lett.,Vol.7,No.2,Web Release Date: 23-Dec-2004,2005.01.
19. M. Tanaka, Y. Demizu, M. Doi, M. Kurihara, and H. Suemune,Chiral Centers in the Side Chain of alpha-Amino Acdis Control the Helical Screw Sense of Peptides,Angew. Chem. Int. Ed.,Vol.43,No.40,43(40), 5360-5363
Selected as VIP & Cover picture.,2004.01.
20. M. Tanaka, E. Toyofuku, Y. Demizu, O. Yoshida, K. Nakazawa, K. Sakai, and H. Suemune,Asymmetric Ring Cleavage Reaction with a Combination of Optically Active Cycloalkane-1,2-diol and Lewis Acid: Application to Formal Synthesis of (-)-Alloyohimbane and Approach to Construction of Adjacent Chiral Quaternary Centers,Tetrahedron,Vol.60,No.10,60 (10), 2271-2281,2004.01.
21. M. Imai, M. Tanaka, K. Tanaka, Y. Yamamoto, N. Imai-Ogata, M. Shimowatari, S. Nagumo, N. Kawahara, and H. Suemune,Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation between Salicylaldehydes and 1,4-Penta- or 1,5-Hexadienes,J. Org. Chem.,Vol.69,No.4,69 (4), 1144-1150,2004.01.
22. M. Tanaka, S. Nishimura, M. Oba, Y. Demizu, M. Kurihara, and H. Suemune,An Extended Planar C5 Conformation and a 310-Helical Structure of
Peptide-Foldamer Composed of Diverse α-Ethylated α,α-Disubstituted
α-Amino Acids,Chemisrty, A European Journal,Vol.9,No.13,9, 3082-3090,2003.09.
23. M. Tanaka, M. Imai, Y. Yamamoto, K. Tanaka, M. Shimowatari, S. Nagumo, N. Kawahara, and H. Suemune,Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation,Org. Lett.,Vol.5,No.8,5 (8), 1365-1367.,2003.04.
24. M. Aso, T. Kaneko, M. Nakamura, N. Koga, H. Suemune,A simple and efficient method for synthesis of 5-substituted 2-deoxyuridine nucleosides using metal-halogen exchange reaction of 5-iodo-2-deoxyuridine sodium salt,Chem. Commun.,No.9,(9) 1094-1095,2003.01.
25. A.Watanabe, T.Kamahori, M.Aso, H.Suemune,Asymmetric synthesis of C2-symmetric 5,6-bis(benzyloxy)cyclohexa-1,3-diene and a tricarbonyliron complex,J. Chem. Soc. Perkin Transactions 1,No.22,2539-2543,2002.01.
26. M. Oba, M. Tanaka, M. Kurihara, and H. Suemune,Conformation of Peptides Containing a Chiral a-Ethylated a,a-Disubstituted a-Amino Acid:(S)-aEthylleucine (= (2S)-2-Amino-2-ethyl-4-methylpentanoic Acid) within Sequences of Dimethylglycine and Diethylglycine Residues,Helv. Chim. Acta,Vol.85,No.10,85(10) 3197-3218,2002.01.
27. M. Aso, T. Ikeno, K. Norihisa, M. Tanaka, N. Koga, and H. Suemune,Molecular Design of a New Class of Spin-Labeled Ribonucleosides with
N-tert-Butylaminoxyl Radicals,J. Org. Chem.,Vol.66,No.10,66 (10), 3513-3520,2001.01.
28. M. Imai, M. Tanaka, and H. Suemune,Insight into the Rh-Catalyzed Cyclization of Dissymmetrically Racemic
(dl)-3,4-Disubstituted 4-Pentenal: Regio-, Diastereo-, Enantioselectivity, and Kinetic Resolution,Tetrahedron,Vol.57,No.7,1205-1211,2001.01.
29. M. Tanaka, M. Takahashi, M. Fujio, K. Funakoshi, K. Sakai, and H. Suemune,Enantio- and Diastereoselective Construction of 4,9-Dimethylspiro[4.4]nonane-2,7-dione Using Rh-catalyzed Asymmetric Cyclization,Tetrahedron,Vol.57,No.7,1197-1204,2001.01.
1. 松崎拓也, 楊 波, 末宗 洋, 麻生 真理子,Introduction of bioorthogonal reporters into DNA-Interacting proteins by reactive oligodeoxynucleotides
2. 潟永ちえみ, 楊 波, 末宗 洋, 麻生 真理子,Oligodeoxynucleotides for fluorescent modification of DNA-Interacting protein at lysine residue
Educational Activities
Graduate School:Advanced Organic Chemistry
Undergraduate School: Organic Chemistry III