OKA Natsuhisa

J-GLOBAL         Last updated: Nov 12, 2019 at 14:31
 
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Name
OKA Natsuhisa
Affiliation
Gifu University
Section
Faculty of Engineering
Degree
B.S.(The University of Tokyo), M.S.(The University of Tokyo), Ph.D.(The University of Tokyo)
Research funding number
50401229

Profile

Chemistry of biomolecules, especially nucleic acids and carbohydrates

Research Areas

 
 

Academic & Professional Experience

 
Oct 2016
 - 
Today
Associate Professor, Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN)
 
2009
   
 
- Associate Professor, Department of Chemistry (2013- Department of Chemistry and Biomolecular Science), Faculty of Engineering, Gifu University
 
2005
 - 
2009
Assistant Professor, Graduate School of Frontier Sciences, The University of Tokyo
 
2004
 - 
2005
Postdoctral fellow, Johns Hopkins University
 
2003
 - 
2004
Postdoctral fellow, University of California, San Diego
 

Education

 
Apr 1994
 - 
Mar 1996
The University of Tokyo
 
Apr 1996
 - 
Mar 1998
Department of Chemistry and Biotechnology, The University of Tokyo
 
Apr 1998
 - 
Mar 2000
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
 
Apr 2000
 - 
Mar 2003
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
 

Awards & Honors

 
2013
Ajinomoto Award in Synthetic Organic Chemistry, Japan
Winner: Natsuhisa Oka
 
2011
Incentive Award for Young Scientist, Tokai branch of The Society of Synthetic Organic Chemistry, Japan
Winner: Natsuhisa Oka
 

Published Papers

 
Oka, N.; Ito, K.; Ando, K.
Malaysian J. Anal. Sci.   23(4) 648-653   Aug 2019   [Refereed]
Oka, N.; Mori, A.; Ando, K.
Eur. J. Org. Chem.   6355-6362   Sep 2018   [Refereed]
Oka, N.; Fukuta, A.; Ando, K.
Tetrahedron   74 5709-5714   2018   [Refereed]
Oka, N.; Ori, K.; Ando, K.
Phosphorus, Sulfur Silicon Relat. Elem.   192(4) 454-463   2017   [Refereed]
Oka, N.; Wada, T.
J. Synth. Org. Chem. Jpn.   74(1) 31-44   Jan 2016   [Refereed][Invited]
Nukaga, Y.; Takemura, T.; Iwamoto, N.; Oka, N.; Wada, T.
RSC Adv.   5 2392-2395   2015   [Refereed]
Oka, N.; Kajino, R.; Takeuchi, K.; Nagakawa, H.; Ando, K.
J. Org. Chem.   79 7656-7664   2014   [Refereed]
Uehara, S.; Hiura, S.; Higashida, R.; Oka, N.; Wada, T.
J. Org. Chem.   79 3465-3472   2014   [Refereed]
Oka, N.; Morita, Y.; Itakura, Y.; Ando, K.
Chem. Commun.   49 11503-11505   2013   [Refereed]
Tatsumi, S.; Matsumura, F.; Oka, N.; Wada, T.
Tetrahedron Lett.   54(29) 3731   2013   [Refereed]
Oka, N.; Murakami, R.; Kondo, T.; Wada, T.
J. Fluorine Chem.   150 85-91   2013   [Refereed]
Nomura, Y.; Onda, Y.; Ohno, S.; Taniguchi, H.; Ando, K.; Oka, N.; Nishikawa, K.; Yokogawa, T.
Protein Expr. Purif.   88(1) 13-19   2013   [Refereed]
Oka, N.; Ito, K.; Tomita, F.; Ando, K.
Chem. Lett.   41(12) 1630-1632   2012   [Refereed]
Nukaga, Y.; Yamada, K.; Ogata, T.; Oka, N.; Wada, T.
J. Org. Chem.   77(18) 7913-7922   2012   [Refereed]
Oka, N.; Sato, K.; Wada, T.
Trends in Glycoscience and Glycotechnology   24(138) 152-168   Jul 2012   [Refereed]
Oka, N.; Takayama, Y.; Ando, K.; Wada, T.
Bioorg. Med. Chem. Lett.   22(14) 4571-4574   Jun 2012   [Refereed]
Iwamoto, N.; Oka, N.; Wada, T.
Tetrahedron Lett.   53(33) 4361-4364   Jun 2012   [Refereed]
Fujita, S.; Oka, N.; Matsumura, F.; Wada, T.
J. Org. Chem.   76(8) 2648-2659   2011   [Refereed]
Uchiyama, N.; Ogata, T.; Oka, N.; Wada, T.
Nucleosides Nucleotides Nucleic Acids   30 446-456   2011   [Refereed]
Oka, N.; Wada, T.
Chem. Soc. Rev.   40(12) 5829-5843   2011   [Refereed][Invited]
Oka, N.; Maizuru, Y.; Shimizu, M.; Wada, T.
Nucleosides, Nucleotides, and Nucleic Acids   29(2) 144-154   2010
Matsumura, F.; Tatsumi, S.; Oka, N.; Wada, T.
Carbohydrate Research   345(9) 1211-1215   2010
Nagata, S.; Hamasaki, T.; Uetake, K.; Masuda, H.; Takagaki, K.; Oka, N.; Wada, T.; Ohgi, T.; Yano, J.
Nucleic Acids Research   38(21) 7845-7857   2010
Oka, N.; Kondo, T.; Fujiwara, S.; Maizuru, Y.; Wada, T.
11(4) 967-970   2009
Higashida, R.; Oka, N.; Kawanaka, T.; Wada, T.
Chemical Communications   (18) 2466-2468   2009
Oka, N.; Nakamura, M.; Soeda, N.; Wada, T.
694(14) 2171-2178   2009
Matsumura, Fumiko; Oka, Natsuhisa; Wada, Takeshi
Organic Letters   10(8) 1557-1560   2008
Enya, Yukiko; Nagata, Seigo; Masutomi, Yutaka; Kitagawa, Hidetoshi; Takagaki, Kazuchika; Oka, Natsuhisa; Wada, Takeshi; Ohgi, Tadaaki; Yano, Junichi.
Bioorganic & Medicinal Chemistry   16(20) 9154-9160   2008
Oka, N.; Yamamoto, M.; Sato, T.; Wada, T.
Journal of the American Chemical Society   130(47) 16031-16037   2008
Watanabe, Kazunori; Toh, Yukimatsu;Suto, Kyoko; Shimizu, Yoshihiro; Oka, Natsuhisa; Wada, Takeshi; Tomita, Kozo
Nature   449(7164) 867-871   2007
Kato, Yukiko; Oka, Natsuhisa; Wada, Takeshi.
Tetrahedron Letters   47(15) 2501-2505   2006
Wada, Takeshi; Maizuru, Yukihiro; Shimizu, Mamoru; Oka, Natsuhisa; Saigo, Kazuhiko.
Bioorganic & Medicinal Chemistry Letters   16(12) 3111-3114   2006
Imoto, Shuhei.; Patro, Jennifer N.; Jiang, Yu Lin; Oka, Natsuhisa; Greenberg, Marc M.
Journal of the American Chemical Society   128(45) 14606-14611   2006
Oka, Natsuhisa; Greenberg, Marc M.
Nucleic Acids Res.   33(5) 1637-1643   2005
1,2-Ethylene-3,3-bis(4',4''-dimethoxytrityl chloride) (E-DMT): Synthesis and Applications of a Novel Protecting Reagent.
Oka, Natsuhisa; Sanghvi, Yogesh S.; Theodorakis, Emmanuel A.
Synlett   (5) 823-826   2004
Oka, Natsuhisa; Sanghvi, Yogesh S.; Theodorakis, Emmanuel A.
Bioorganic & Medicinal Chemistry Letters   14(12) 3241-3244   2004
Shimizu, Mamoru; Wada, Takeshi; Oka, Natsuhisa; Saigo, Kazuhiko.
Journal of Organic Chemistry   69(16) 5261-5268   2004
Oka, Natsuhisa; Wada, Takeshi; Saigo, Kazuhiko.
Journal of the American Chemical Society   125(27) 8307-8317   2003
Oka, Natsuhisa; Wada, Takeshi; Saigo, Kazuhiko.
Journal of the American Chemical Society   124(18) 4962-4963   2002
Wada, Takeshi; Shimizu, Mamoru; Oka, Natsuhisa; Saigo, Kazuhiko.
Tetrahedron Letters   43(23) 4137-4140   2002
Application of cis-2-Amino-3, 3-Dimethy1-1-Indanol as an Efficient Chiral Auxiliary to the Asymmetric Ireland-Claisen Rearrangement. Improvement of the Diastereoselectivity by Combinational Use of Chlorodimethylsilane as a Silylating Agent
Matsui, Satoshi; Oka, Natsuhisa; Hashimoto, Yukihiko; Saigo, Kazuhiko.
Enantiomer   5 105-108   2000
Fujita, S.; Oka, N.; Matsumura, F.; Wada, T.
The Journal of Organic Chemistry   76(8) 2648-2659   2011
Uchiyama, N.; Ogata, T.; Oka, N.; Wada, T.
Nucleosides, Nucleotides, and Nucleic Acids   in press   2011
Sato, K.; Oka, N.; Fujita, S.; Matsumura, F.; Wada, T.
The Journal of Organic Chemistry   75(7) 2147-2156   2010
Matsumura, F.; Tatsumi, S.; Oka, N.; Wada, T.
Carbohydrate Research   345(9) 1211-1215   2010
Nagata, S.; Hamasaki, T.; Uetake, K.; Masuda, H.; Takagaki, K.; Oka, N.; Wada, T.; Ohgi, T.; Yano, J.
Nucleic Acids Research   38(21) 7845-7857   2010
Iwamoto, N.; Oka, N.; Sato, T.; Wada, T.
Angew. Chem. Int. Ed.   48(3) 496-499   2009
Oka, N.; Kondo, T.; Fujiwara, S.; Maizuru, Y.; Wada, T.
Org. Lett.   11 967–970   2009
Higashida, R.; Oka, N.; Kawanaka, T.; Wada, T.
Chem. Commun.   (18) 2466-2468   2009
Oka, N.; Nakamura, M.; Soeda, N.; Wada, T.
J. Organomet. Chem.   694(14) 2171-2178   2009
Matsumura, Fumiko; Oka, Natsuhisa; Wada, Takeshi
Organic Letters   10(8) 1557-1560   2008
Enya, Y.; Nagata, S.; Masutomi, Y.; Kitagawa, H.; Takagaki, K.; Oka, N.; Wada, T.; Ohgi, T.; Yano, J.9154–9160
Bioorg. Med. Chem.   20 9154–9160   2008
Watanabe, Kazunori; Toh, Yukimatsu; Suto, Kyoko; Shimizu, Yoshihiro; Oka, Natsuhisa; Wada, Takeshi; Tomita, Kozo
Nature   449(7164) 867-871   2007
Kato, Yukiko; Oka, Natsuhisa; Wada, Takeshi.
Tetrahedron Letters   47(15) 2501-2505   2006
Wada, Takeshi; Maizuru, Yukihiro; Shimizu, Mamoru; Oka, Natsuhisa; Saigo, Kazuhiko.
Bioorganic & Medicinal Chemistry Letters   16(12) 3111-3114   2006
Imoto, Shuhei.; Patro, Jennifer N.; Jiang, Yu Lin; Oka, Natsuhisa; Greenberg, Marc M.
Journal of the American Chemical Society   128(45) 14606-14611   2006
Oka, Natsuhisa; Greenberg, Marc M.
Nucleic Acids Research   33(5) 1637-1643   2005
1,2-Ethylene-3,3-bis(4',4''-dimethoxytrityl chloride) (E-DMT): synthesis and applications of a novel protecting reagent.
Oka, Natsuhisa; Sanghvi, Yogesh S.; Theodorakis, Emmanuel A.
Synlett   (5) 823-826   2004
Oka, Natsuhisa; Sanghvi, Yogesh S.; Theodorakis, Emmanuel A.
Bioorganic & Medicinal Chemistry Letters   14(12) 3241-3244   2004
Shimizu, Mamoru; Wada, Takeshi; Oka, Natsuhisa; Saigo, Kazuhiko.
Journal of Organic Chemistry   69(16) 5261-5268   2004
Oka, Natsuhisa; Wada, Takeshi; Saigo, Kazuhiko.
Journal of the American Chemical Society   125(27) 8307-8317   2003
Oka, Natsuhisa; Wada, Takeshi; Saigo, Kazuhiko.
Journal of the American Chemical Society   124(18) 4962-4963   2002
Wada, Takeshi; Shimizu, Mamoru; Oka, Natsuhisa; Saigo, Kazuhiko.
Tetrahedron Letters   43(23) 4137-4140   2002
Application of cis-2-amino-3,3-dimethyl-1-indanol as an efficient chiral auxiliary to the asymmetric Ireland-Claisen rearrangement. Improvement of the diastereoselectivity by combinational use of chlorodimethylsilane as a silylating agent.
Matsui, Satoshi; Oka, Natsuhisa; Hashimoto, Yukihiko; Saigo, Kazuhiko.
Enantiomer   5(1) 105-108   2000

Misc

 
T. Wada, M. Shimizu, N. Oka, K. Saigo
Nucleic acids symposium series   135-136   Jan 2000
Deoxyribonucleoside 3'-boranophosphate derivatives including adenine, cytosine, guanine, and thymine bases were synthesized in good yields by the use of a new boranophosphorylation reaction. The reaction was found to be effective for the formation...
Takeshi Wada, Tomoaki Kondo, Satoshi Fujiwara, Terutoshi Sato, Natsuhisa Oka
Nucleic acids symposium series (2004)   119-120
Stereoregulated oligoribonucleoside phosphorothioates were synthesized by the use of 2'-O-TBDMS-protected ribonucleoside 3'-O-oxazaphospholidine derivatives as monomers and N-(cyanomethyl)ammonium salts as activators. Diastereoselectivity of the c...
Natsuhisa Oka, Renpei Higashida, Yuji Takayama, Kaori Ando, Takeshi Wada
Nucleic acids symposium series (2004)   111-112   May 2011
Nucleoside H-boranophosphonates were synthesized via the condensation reactions of appropriately protected nucleosides with monopyridinium H-boranophosphonate and subsequent deprotection under basic conditions. 3',5'-O-Protected dinucleoside H-bor...
Natsuhisa Oka, Takeshi Wada, Takeshi Wada, Kazuhiko Saigo, Kazuhiko Saigo
Nucleosides, Nucleotides and Nucleic Acids   22 1411-1413
Dialkyl(cyanomethyl)ammonium salts 1 were synthesized and used as a novel class of activators for the stereospecific condensations of diastereopure nucleoside 3′-O-oxazaphospholidines with a nucleoside. This new oxazaphospholidine method could eff...
Renpei Higashida, Toshihide Kawanaka, Natsuhisa Oka, Takeshi Wada
Nucleic acids symposium series (2004)   133-134
Nucleoside H-boranophosphonates were synthesized via the condensation reactions of appropriately protected nucleosides with monopyridinium H-boranophosphonate. The condensation reactions gave only the mono-esterified products under the optimized c...
Takeshi Wada, Takeshi Wada, Natsuhisa Oka, Kazuhiko Saigo
Nucleosides, Nucleotides and Nucleic Acids   22 1431-1433
Reaction mechanisms for the diastereoselective synthesis of deoxyribonucleoside 3′-cyclic phosphoramidites as well as dinucleoside phosphite intermediates by the oxazaphospholidine approach were analyzed by means of ab initio molecular orbital cal...
Takeshi Wada, Natsuhisa Oka, Kazuhiko Saigo
Nucleic acids research. Supplement (2001)   153-154
This paper describes the reaction mechanisms for the stereoselective synthesis of deoxyribnucleoside 3'-cyclic phosphoramidites as well as dinucleoside phosphite derivatives by the oxazaphospholidine approach. All the key reactions in the present ...
Natsuhisa Oka, Mika Yamamoto, Terutoshi Sato, Takeshi Wada
Nucleic acids symposium series (2004)   123-124
An efficient stereocontrolled synthesis of oligodeoxyribonucleoside phosphorothioates on a solid-support by an oxazaphospholidine method was achieved. A detailed investigation on the reagents and conditions for the solid-phase synthesis revealed t...
Naoki Iwamoto, Natsuhisa Oka, Takeshi Wada
Nucleic acids symposium series (2004)   333-334   Dec 2008
Synthesis of stereoregulated backbone-modified oligodeoxyribonucleotides via the corresponding diastereopure H-phosphonate intermediates is described. The diastereopure H-phosphonate intermediates were synthesized by using the nucleoside 3'-oxazap...
Natsuhisa Oka, Yukihiro Maizuru, Mamoru Shimizu, Kazuhiko Saigo, Takeshi Wada
Nucleic acids symposium series (2004)   131-132   Dec 2005
Stereodefined dinucleoside boranophosphates were synthesized from diastereopure nucleoside 3'-oxazaphospholidine derivatives. The new method is based on the stereospecific formation of dinucleoside phosphite intermediates catalyzed by a non-nucleo...
Naoki Iwamoto, Terutoshi Sato, Natsuhisa Oka, Takeshi Wada
Nucleic acids symposium series (2004)   159-160
Stereocontrolled synthesis of H-phosphonate DNA by an oxazaphospholidine approach is described. Diastereopure 2'-deoxynucleoside 3'-oxazaphospholidine monomers having two substituents at the 5-position of the oxazaphospholidine ring were allowed t...
Naoki Iwamoto, Natsuhisa Oka, Takeshi Wada
Nucleic acids symposium series (2004)   9-10   May 2011
P-Stereodefined oligodeoxyribonucleoside boranophosphates (PB-ODNs) were successfully synthesized by the conversion of diastereopure H-phosphonate intermediates. Thermal denaturation studies clearly showed that the duplex stability of PB-ODNs with...
Natsuhisa Oka, Mika Yamamoto, Terutoshi Sato, Takeshi Wada
Nucleic acids symposium series (2004)   335-336   Dec 2008
Solid-phase synthesis of oligonucleotides having a fully-modified stereoregular phosphorothioate backbone or a stereoregular phosphate/phosphorothioate chimeric backbone was achieved by using diastereopure nucleoside 3'-bicyclic oxazaphospholidine...
Takeshi Wada, Natsuhisa Oka, Kazuhiko Saigo
Nucleic acids research. Supplement (2001)   109-110
Stereocontrolled synthesis of oligodeoxyribonucleoside phosphorothioates using nucleoside 3'-O-oxazaphospholidine derivatives as monomer units is described. N-(Cyanomethyl)pyrrolidinium triflate (CMPT) was found to be effective as an activator for...
Takeshi Wada, Satoshi Fujiwara, Terutoshi Sato, Natsuhisa Oka, Kazuhiko Saigo
Nucleic acids symposium series (2004)   57-58
Stereoregulated diribonucleoside phosphorothioates were synthesized by the use of 2'-O-TBDMS-protected ribonucleoside 3'-O-oxazaphospholidine derivatives as monomers and N-(cyanomethyl)ammonium salts as activators. Diastereoselectivity of the cond...
N. Oka, T. Wada, K. Saigo
Nucleic acids research. Supplement (2001)   13-14
Diastereopure nucleoside 3'-cyclic phosphoramidites were synthesized stereoselectively from enantiopure 1,2-amino alcohols. In the presence of a novel activator, these phosphoramidites underwent the condensation with 3'-O-tert-butyldimethylsilylth...
Takeshi Wada, Takeshi Wada, Mamoru Shimizu, Natsuhisa Oka, Kazuhiko Saigo
Nucleosides, Nucleotides and Nucleic Acids   22 1171-1173
Dinucleoside boranophosphates including four kinds of nucleobases were synthesized by a boranophosphotriester method in good yields. In the present boranophosphotriester method, side-reactions at the nucleobases, which caused by a borane reagent, ...

Books etc

 
複合糖質の化学と最新応用技術 第3章 糖-1-リン酸誘導体の化学合成
Jun 2009   

Conference Activities & Talks

 
Stereoselective furanosylation reactions for the synthesis of oligosaccharides and nucleosides [Invited]
Natsuhisa Oka
The 8th International Conference of The Indonesian Chemical Society (ICICS) 2019   7 Aug 2019   
Serendipitous one-step synthesis of cyclopentene derivatives from Julia-Kocienski reagents derived from nucleosides [Invited]
Natsuhisa Oka
3rd International Joint Meeting of AGP   28 Mar 2019   
Stereocontrolled Synthesis of P-Chiral Oligonucleotides [Invited]
OKA Natsuhisa
International Symposium on Pure & Applied Chemistry 2017 (ISPAC 2017)   9 Jun 2017   
Stereocontrolled synthesis of P-chiral oligonucleotide analogs [Invited]
OKA Natsuhisa
1st Joint International Seminar of Faculty of Science and Technology (Universiti Kebangsaan Malaysia) and Faculty of Engineering (Gifu University) 2014 (Gifu University)   1 Aug 2014   
キラルリン(III) 原子の不斉制御によるリン原子修飾核酸の立体選択的合成 [Invited]
Natsuhisa Oka
日本薬学会 第134年会 一般シンポジウム「有機合成化学の若い力:どう捉え、どう創り、どう展開するか」   28 Mar 2014   
リン原子オリゴ修飾核酸の立体選択的合成法の開発 [Invited]
Natsuhisa Oka
第44回中部化学関係学協会支部連合秋季大会   3 Nov 2013   

Research Grants & Projects

 
Ministry of Education, Culture, Sports, Science and Technology: Grants-in-Aid for Scientific Research(若手研究(B))
Project Year: 2008 - 2009    Investigator(s): Natsuhisa OKA
P-Boronated nucleotide analogues have attracted much attention as potential therapeutic agents against various diseases, such as cancer and AIDS. However, only a few kinds of P-boronated nucleotide analogues are currently available. In this projec...
Ministry of Education, Culture, Sports, Science and Technology: Grants-in-Aid for Scientific Research(若手研究(B))
Project Year: 2012 - 2013    Investigator(s): Natsuhisa OKA
In this study, we developed a novel method to synthesize chemically modified analogs of inosine 6-phosphates, which are observed in the biosynthesis of nucleotides. For this purpose, we applied a non-nucleophilic acidic activator, N-(cyanomethyl)d...
Stereocontrolled synthesis of backbone-modified DNA analogs.
Grant-in-Aid for Scientific Research
Project Year: 2006 - 2007