Fujie Tanaka, Ph.D.

Associate Professor

E-mail: ftanaka at oist.jp  

Education

B.S., Gifu Pharmaceutical University
Ph.D., Kyoto University
 

Awards

Achievement Award of the Society of Japanese Women Scientists (2009)
Kansai Regional Award of The Society of Synthetic Organic Chemistry, Japan (2010)
 

Research Career

Fujie Tanaka received her Ph.D. in 1992 from Kyoto University (Graduate School of Pharmaceutical Science).  After postdoctoral studies in the Frontier Research Program at Riken (Saitama, Japan) and at Protein Engineering Research Institute (Biomolecular Engineering Research Institute) (Osaka, Japan), she joined The Scripps Research Institute as a Research Associate (La Jolla, USA).  She was appointed Assistant Professor at The Scripps Research Institute in 2000 and was promoted to Associate Professor in 2007.  In 2011, she was appointed Associate Professor at the Okinawa Institute of Science and Technology Graduate University (OIST).

 

Selected Publications

 Selected, 2013-

Chouthaiwale, P. V.; Tanaka, F. Reactions of pyruvates: organocatalytic synthesis of functionalized dihydropyrans in one pot and further transformations to functionalized carbocycles and heterocycles. Chem. Commun. 2014, 50, 14881-14884.

Cui, H.-L.; Tanaka, F. One-pot synthesis of polysubstituted 3-acylpyrroles by cooperative catalysis. Org. Biomol. Chem. 2014, 12, 5822-5826.

Zhang, D.; Johnson, S.; Cui, H.-L.; Tanaka, F. Synthesis of furanose spirooxindoles via 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed aldol reactions of a pyruvic aldehyde derivative. Asian J. Org. Chem. 2014, 3, 391-394.

Mase, N.; Ando, T.; Shibagaki, F.; Sugita, A.; Narumi, T.; Toda, M.; Watanabe, N.; Tanaka, F. Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO. Tetrahedron Lett. 2014, 55, 1946-1948.

Katsuyama, I.; Chouthaiwale, P. V.; Akama, H.; Cui, H.-L.; Tanaka, F. Fluorogenic probes for aldol reactions: Tuning of fluorescence using p-conjugation systems. Tetrahedron Lett. 2014, 55, 74-78.

Mase, N.; Takabe, K.; Tanaka, F. Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence. Tetrahedron Lett. 2013, 54, 4306-4308; erratum 2013, 54, 5140.

Cui, H.-L.; Tanaka, F. Catalytic enantioselective formal hetero-Diels-Alder reactions of enones with isatins to give spirooxindole tetrahydropyranones. Chem. Eur. J. 2013, 19, 6213-6216; corrigendum 2013, 19, 12187.

Katsuyama, I.; Chouthaiwale, P. V.; Cui, H.-L.; Ito, Y.; Sando, A.; Tokiwa, H.; Tanaka, F. Substituent-dependent reactivity in aldehyde transformations: 4-(phenylethynyl)benzaldehydes versus simple benzaldehydes. Tetrahedron 2013, 69, 4098-4104.

 

Selected, Before 2013, Primary Publications

Guo, H.-M.; Tanaka, F. A fluorogenic aldehyde bearing a 1,2,3-triazole moiety for monitoring the progress of aldol reactions.  J. Org. Chem. 2009, 74, 2417-2424.

Minakawa, M.; Guo, H.-M.; Tanaka, F.  Imines that react with phenols in water over a wide pH range. J. Org. Chem. 2008, 73, 8669-8672.

Guo, H.-M.; Minakawa, M.; Tanaka, F.  Fluorogenic imines for fluorescent detection of Mannich-type reactions of phenols in water. J. Org. Chem. 2008, 73, 3964-3966.

Jiang, L.; Althoff, E. A.; Clemente, F. R.; Doyle, L.; Rothlisberger, D.; Zanghellini, A.; Gallahe, J. L.; Betker, J. L.; Tanaka, F.; Barbas, C. F., III; Hilvert, D.; Houk, K. N.; Stoddard, B.; Baker, D.  De novo computational design of retro-aldol enzymes. Science 2008, 319, 1387-1391.

Zhang, H.; Mitsumori, S.; Utsumi, N.; Imai, M.; Garcia-Delgado, N.; Mifsud, M.; Albertshofer, K.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III.  Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: Importance of the 3-acid group on pyrrolidine for stereocontrol. J. Am. Chem. Soc. 2008, 130, 875-886.

Ramasastry, S. S. V.; Albertshofer, K.; Utsumi, N.; Tanaka, F.; Barbas, C. F., III.  Mimicking fructose and rhamnulose aldolases: Organocatalytic syn-aldol reactions with unprotected dihydroxyacetone. Angew. Chem., Int. Ed. 2007, 46, 5572-5575.

Tanaka, F.; Fuller, R.; Asawapornmongkol, L.; Warsinke, A.; Gobuty, S.; Barbas, C. F., III.  Development of a small peptide tag for covalent labeling of proteins. Bioconjugate Chem. 2007, 18, 1318-1324.

Utsumi, N.; Zhang, H.; Tanaka, F.; Barbas, C. F., III.  A way to highly enantiomerically enriched aza-Morita-Baylis-Hillman-type products. Angew. Chem., Int. Ed. 2007, 46, 1878-1880.

Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F., III.  Direct catalytic asymmetric synthesis of anti-1,2-amino alcohols and syn-1,2-diols through organocatalytic anti-Mannich and syn-aldol reactions. J. Am. Chem. Soc. 2007, 129, 288-289.

Zhang, H.; Mifsud, M.; Tanaka, F.; Barbas, C. F., III.  3-Pyrrolidinecarboxylic acid for direct catalytic asymmetric anti-Mannich-type reactions of unmodified ketones. J. Am. Chem. Soc. 2006, 128, 9630-9631.

Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III.  Organocatalytic direct asymmetric aldol reactions in water. J. Am. Chem. Soc. 2006, 128, 734-735.

Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III.  Direct asymmetric anti-Mannich-type reactions catalyzed by a designed amino acid. J. Am. Chem. Soc. 2006, 128, 1040-1041.

Tanaka, F.; Fuller, R.; Barbas, C. F., III.  Development of small designer aldolase enzymes: Catalytic activity, folding, and substrate specificity. Biochemistry 2005, 44, 7583-7592.

Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III.  Direct organocatalytic asymmetric aldol reactions of α-amino aldehydes: expedient syntheses of highly enantiomerically enriched anti-β-hydroxy-α-amino acids. Org. Lett. 2004, 6, 3541-3544.

Tanaka, F.; Mase, N.; Barbas, C. F., III.  Design and use of fluorogenic aldehydes for monitoring the progress of aldehyde transformations. J. Am. Chem. Soc. 2004, 126, 3692-3693.

Mase, N.; Tanaka, F.; Barbas, C. F., III.  Synthesis of b-hydroxyaldehydes with stereogenic quaternary carbon centers by direct organocatalytic asymmetric aldol reactions. Angew. Chem., Int. Ed. 2004, 43, 2420-2423.

Tanaka, F.; Fuller, R.; Shim, H.; Lerner, R. A.; Barbas, C. F., III.  Evolution of aldolase antibodies in vitro: correlation of catalytic activity and reaction-based selection. J. Mol. Biol. 2004, 335, 1007-1018.

Tanaka, F.; Thayumanavan, R.; Mase, N.; Barbas, C. F., III.  Rapid analysis of solvent effects on enamine formation by fluorescence: how might enzymes facilitate enamine chemistry with primary amines? Tetrahedron Lett. 2004, 45, 325-328.

Mase, N.; Tanaka, F.; Barbas, C. F., III.  Rapid fluorescent screening for bifunctional amine-acid catalysts: efficient syntheses of quaternary carbon containing aldols under organocatalysis. Org. Lett. 2003, 5, 4369-4372.

Tanaka, F.; Thayumanavan, R.; Barbas, C. F., III.  Fluorescent detection of carbon-carbon bond formation. J. Am. Chem. Soc. 2003, 125, 8523-8528.

Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III.  One-pot asymmetric synthesis of β-cyanohydroxymethyl α-amino acid derivatives: Formation of three contiguous stereogenic centers. Org. Lett. 2002, 4, 4519-4522.

Thayumanavan, R.; Dhevalapally, B.; Sakthivel, K.; Tanaka, F.; Barbas, C. F., III.  Amine-catalyzed direct Diels-Alder reactions of α,β-unsaturated ketones with nitro olefins. Tetrahedron Lett. 2002, 43, 3817-3820.

Tanaka, F.; Barbas, C. F., III.  A modular assembly strategy for improving the substrate specificity of small catalytic peptides. J. Am. Chem. Soc. 2002, 124, 3510-3511.

Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III.  A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives. J. Am. Chem. Soc. 2002, 124, 1866-1867.

Tanaka, F.; Lerner, R. A.; Barbas, C. F., III.  Reconstructing aldolase antibodies to alter their substrate specificity and turnover. J. Am. Chem. Soc. 2000, 122, 4835-4836.

Tanaka, F.; Kinoshita, K.; Tanimura, R.; Fujii, I.  Relaxing substrate specificity in antibody-catalyzed reactions: Enantioselective hydrolysis of N-Cbz-amino acid esters. J. Am. Chem. Soc. 1996, 118, 2332-2339.

Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K.  1,1'-Binaphthalene-2,2'-diol as a chiral auxiliary.  Diastereoselective alkylation of binaphthyl esters, complex-induced proximity effects in enolate formation, and one step synthesis of an optically active b-substituted ketone. J. Am. Chem. Soc. 1995, 117, 12159-12171.

 

Selected, Before 2013, Reviews

Tanaka, F. Enamine-based reactions: Strategies for the development of organocatalysts and catalyzed reactions. Journal of the Society of Japanese Women Scientists 2009, 10, 1-9.

Notz, W.; Tanaka, F.; Barbas, C. F., III. Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric aldol, Mannich, Michael, and Diels-Alder reactions. Acc. Chem. Res. 2004, 37, 580-591.

Tanaka, F. Catalytic antibodies as designer proteases and esterases. Chem. Rev. 2002, 102, 4885-4906.