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Laboratory for Functional Photochemistry and Chemicalbiology
Division of Materials Design,
Institute of Multidisciplinary Research for Advanced Materials,
Tohoku University

Takehiko WADA (Professor)

Yasuyuki Araki (Research associate)

Seiji Sakamoto (Research associate)

Established recently in 2007, our research group at Tohoku University consists of one tenured and two tenure-track investigators, Takehiko WADA (professor; tenured) and Yasuyuki ARAKI (research associate; tenure-track), Seiji SAKAMOTO (research associate; tenure-track), Yoko GOTO (a secretary), and nine graduate students.

Focusing our reseach interest mostly on the recognition and complexation behavior control of bioplymrs, such as DNA/RNA, proteines and so on. Another topics are reaction control based on molecular recognition phenomena in both ground and electronically excited states, we are pursuing mechanistic and synthetic studies on asymmetric photochemistry with supramolecular biopolymers as chiral reaction fields.

Recent publications

Original Papers

2007

143. Highly Enantiomeric Supramolecular [4+4] Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Human Serum Albumin,
M. Nishijima, T. Wada, T. Mori, T. C. S. Pace, C. Bohne, and Y. Inoue,
J. Am. Chem. Soc. in pess.
142. Supramolecular Photochirogenesis with Biomolecules. Mechanistic Studies on the Enantiodifferentiation for the Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Bovine Serum Albumin,
M. Nishijima, T. Wada, T. C. S. Pace, A. Nakamura, T. Mori, C. Bohne, and Y. Inoue,
J. Org. Chem. in press (Cover picture).
141. Inherently Chiral Molecular Clips: Synthesis, Chiroptical Properties, and Application to Chiral Discrimination,
G. Fukuhara, S. Madenci, J. Polkowska, F. Bastkowski, F. Klener, Y. Origane, M. Kaneda, T. Mori, T. Wada, and Y. Inoue,
Chem.-Eur. J. in press (Cover picture).
140. Enhanced Ternary 1:2 Host-Guest Complexation of Amino--cyclodextrins with 2-Anthracene- carboxylic Acid,
C. Yang, G. Fukuhara, A. Nakamura, Y. Origane, T. Mori, T. Wada, and Y. Inoue,
J. Inclusion Phenom. Macrocyclic Chem. in press.
139. Pharmacological Activity and Structural Analysis of a Benzamide (TKS159) and Its Optical Isomers in an In Vitro Study and in an In Vivo Study in Mice,
J. Mizoguchi, T. Yanagi, K. Anzai, K. Kodama, O. Kamoda, C. Kamei, N. Kanehisa, Y. Kai, T. Wada, and Y. Inoue,
Methods Find. Exper. Clin. Pharm. (Methods and Findings in Experimental and Clinical Pharmacology), in press.
138. Active Control of DNA Recognition Behavior of -Peptide Ribonucleic Acids Containing Basic Amino Acid Residues by External Factors,
T. Wada, H. Sato, M. Kikkawa, and Y. Inoue,
Biopolym., in press.
137. DNA Recognition and Recognition Control of -Peptide Ribonucleic Acids by External Factors.
T. Wada, M. Kikkawa, H. Sato, and Y. Inoue,
Nucleic Acids Res., in press.
136. Regioselective [2 + 2]-photocycloaddition reactions of chiral tetronates-influence of temperature, pressure, and reaction medium,
M. Fleck, C. Yang, T. Wada, Y. Inoue, T. Bach,
Chem. Comm., 822 (2007).

2006

135. Synthesis of peptide ribonucleic acids (PRNA) - DNA chimera and control of RNase H activity by external factor.
T. Wada, Y. Maeda, N. Sawa, H. Sato, H. Chon, S. Kanaya, Y. Inoue,
Peptide Sci. 222 (2006).
134. Entropy-Controlled Supramolecular Photochirogenesis: Enantiodifferentiating Z-E Photoisomerization of Cyclooctene Included and Sensitized by Permethylated 6-O-Modified -Cyclodextrins,
G. Fukuhara, T. Mori, T. Wada, and Y. Inoue,
J. Org. Chem., 71, 8233 (2006).
133. Enantio-Differentiating Photo-Cyclodimerization of 2-Anthracene-Carboxylic Acid Mediated by ]Cyclodextrins with a Flexible or Rigid Cap,
C. Yang, A. Nakamura, T. Wada, and Y. Inoue,
Org. Lett., 8, 3005 (2006).
132. Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid Using a Chiral N-(2-Hydroxymethyl-4-pyrrolidinyl)benzamide Template,
J. Mizoguchi, Y. Kawanami, T. Wada, K. Kodama, K. Anzai, T. Yanagi, and Y. Inoue,
Org. Lett., 8, 6051 (2006).
131. RNA Recognition and Recognition Control of -Peptide Ribonucleic Acids Containing Arginine Residue by External Factors,
T. Wada, Y. Maeda, N. Sawa, H. Sato, S. Futaki, and Y. Inoue,
Nucleic Acid Res., Sym. Ser, 75 (2006).
130. Solvent switching of stereoselectivity in [4 + 4] photocyclodimerization of 2-anthracenecarboxylic acid,
J. Mizoguchi, T. Wada, and Y. Inoue,
Chem. Lett. 35, 738 (2006).
129. Enantio-Differentiating Photo-Cyclodimerization of 2-Anthracene-Carboxylic Acid Mediated by ]Cyclodextrins with a Flexible or Rigid Cap,
C. Yang, A. Nakamura, T. Wada, and Y. Inoue,
Org. Lett., 8, 3005 (2006).
128. The first supramolecular photosensitization of enantiodifferentiating bimolecular reaction: anti-Markovnikov photoaddition of methanol to 1,1-diphenylpropene sensitized by modified -cyclodextrin,
G. Fukuhara, T. Mori, T. Wada, and Y. Inoue,
Chem. Comm., 1712 (2006).
127. Switching of Product's Chirality in Diastereodifferentiating [2+2] Photocycloaddition of (E)- versus (Z)-Stilbene to Chiral Fumarate upon Direct and Charge-Transfer-Band Excitation,
H. Saito, T. Mori, T. Wada, and Y. Inoue,
Org. Lett., 8, 1909 (2006).
126. Pressure and Temperature-Controlled Enantio-Differentiating [4+4]-Photo-Cyclodimerization of 2-Anthracene-carboxylate Mediated by Secondary Face- and Skeleton-Modified ]Cyclodextrins,
C. Yang, A. Nakamura, G. Fukuhara, Y. Origane, T. Mori, T. Wada, and Y. Inoue,
J. Org. Chem., 71, 3126 (2006).
125. Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra,
T. Furo, T. Mori, Y. Origane, T. Wada, H. Izumi, and Y. Inoue,
Chirality, 18, 205 (2006).
124. New Insights into the Geometry of Resorc[4]arenes: Solvent-Mediated Supramolecular Conformational and Chiroptical Control,
C. Schiel, G. A. Hembury, V. V. Borovkov, M. Klaes, C. Agena, T. Wada, S. Grimme, Y. Inoue, and J. Mattay,
J. Org. Chem. 71, 976 (2006).

2005

123. Absolute Configuration of Chiral [2.2]Paracyclophanes with Intramolecular Charge-Transfer Interaction. Failure of the Exciton Chirality Method and Use of the Sector Rule Applied to the Cotton Effect of the CT Transition.
T. Furo, T.Mori, T.Wada, and Y.Inoue,
J. Am. Chem. Soc. 127, 8242 (2005).
122. Entropy-controlled supramolecular photochirogenesis: enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl--cyclodextrin.
G.Fukuhara, T.Mori, T. Wada, and Y.Inoue,
Chem. Comm., 4199 (2005).
121. Peptide ribonucleic acids (PRNA): novel strategy for active control of DNA recognition by external factors.
T. Wada and Y. Inoue,
Proteins, Nucleic Acids, Enzyme, 50, 463 (2005).
120. Supramolecular photochirogenesis in sensitizing chiral nanopore: Enantiodifferentiating photoisomerization of (Z)-cyclooctene included and sensitized by POST-1.
Y.Gao, T. Wada, K.Yang, K. Kim, and Y.Inoue,
Chirality, 17, 19 (2005).
119. Enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate catalyzed by 6A,6X-diamino-6A,6X-dideoxy--cyclodextrins: Manipulation of product chirality by electrostatic interaction, temperature and solvent in supramolecular photochirogenesis.
C.Yang, G.Fukuhara, A.Nakamura, Y.Origane, K.Fujita, T.Wada, and Y.Inoue,
J. Photochem. Photobio.,A:, 173, 375 (2005).
118. Diastereomeric Molecular Recognition and Binding Behavior of Bile Acids by L/D-Tryptophan-Modified -Cyclodextrins.
Y.Liu, H.Wang, R.Cao,T.Wada, and Y. Inoue,
J. Org. Chem., 70, 8703 (2005).
117. Mechanism of photoisomerization of optically pure trans-2,3-diphenylcyclopropane-1-carboxylic acid derivatives.
J.Sivaguru, T.Wada, Y.Inoue, and V.Ramamurthy, V.
Photochem. Photobio. Sci., 4, 119 (2005).
116. Functionalization of PNA - novel strategy for active control of DNA recognition by external factors using peptide ribonucleic acids (PRNA),
T. Wada and Y. Inoue,
Yuki Gosei Kagaku Kyokaishi 63, 63 (2005).

2004

115.Supramolecular asymmetric photoreactions.
T.Wada and Y.Inoue,
Mol.Supramol.Photochem.11,341 (2004).
114. Synthesis of Peptide Ribonucleic Acid Consisting of D- and L--Glutamic Acid as a Backbone Structure,
T. Wada, Y. Hashimoto, H. Sato, and Y. Inoue,
Nucleic Acids Res., 32, 27-28 (2004).
113. Diastereoselective [2 + 2] Photocycloaddition of Stilbene to Chiral Fumarate. Direct versus Charge-Transfer Excitation,
H. Saito, T. Mori, T. Wada, and Y. Inoue,
J. Am. Chem. Soc., 126, 1900 (2004).
112. Enantiodifferentiating Photoaddition of Alcohols to 1,1-Diphenylpropene in Supercritical Carbon Dioxide: Sudden Jump of Optical Yield at the Critical Density,
Y. Nishiyama, M. Kaneda, R. Saito, T. Mori, T. Wada, and Y. Inoue,
J. Am. Chem. Soc., 126, 6568 (2004).
111. A 5'-Amino-5'-deoxyribonucleoside Containing Nucleic Acid Model for External Reversible Control of Recognition Behavior through anti-syn Orientational Switching of the Nucleobase Induced by Borate Esterification of the cis-2',3'-Diol,
T.Wada, H. Sato, N. Minamimoto, and Y. Inoue,
Biopolym., 76, 15 (2004).
110. Active control of DNA recognition behavior of -peptide ribonucleic acids containing basic amino acid residues by external factors,
T. Wada Y. Inoue,
Polym. Prep., 45, 447 (2004).
109. Pressure control of enantiodifferentiating polar addition of 1,1-diphenylpropene sensitized by chiral Naphthalenecarboxylates,
M. Kaneda, Y. Nishiyama, S. Asaoka, T. Mori, T. Wada, and Y. Inoue,
Org. Biomol. Chem., 2, 1295 (2004).
108. Residue- and sequence-selective binding of nonaromatic dipeptides by bis(-cyclodextrin) with a functional tether,
Y. Liu, Y. Yang, Y. Song, H. Zhang, T. Wada, and Y. Inoue,
Chem. Bio. Chem., 5, 868 (2004).
107. Enhanced Diastereoselectivity via Confinement: Diastereoselective Photoisomerization of 2,3-Diphenyl-1-benzoylcyclopropane Derivatives within Zeolites,
J. Sivaguru, B. Raghavan. T. Wada, Y. Origane, Y. Inoue, and V. Ramamurthy,
J. Org. Chem., 69, 5528 (2004).
106. Enhanced Diastereoselectivity via Confinement: Photoisomerization of 2,3-Diphenylcyclopropane-1-carboxylic Acid Derivatives within Zeolites,
J. Sivaguru, B. Raghavan. T. Wada, Y. Origane, Y. Inoue, and V. Ramamurthy,
J. Org. Chem., 69, 6533 (2004).
105. Enantioselective [4+2]-cycloaddition reaction of a photochemically generated O-quinodimethane: Mechanistic details, association studies, and pressure effects,
B. Grosch, C. Orlebar, M. Kaneda, T. Wada, Y. Inoue, and T. Bach,
Chem. -A Eur. J., 10, 2179 (2004).
104. Active control of DNA recognition behavior of -peptide ribonucleic acids containing basic amino acid residues by external factors,
H. Sato, T. Wada, and Y. Inoue,
J. Bioactive and Compatible Polym., 19, 65 (2004).
103. Pressure control of diastereodifferentiating [2 + 2] photocycloaddition of (E)-stilbene to chiral fumarate upon direct and charge-transfer excitation,
H. Saito, T. Mori, T. Wada, and Y. Inoue,
Chem. Comm., 1652 (2004).
102. Remarkable differences in photo and thermal (acid-catalyzed) reactivities between ortho- and para-acylcyclohexadienones as essential factors determining the overall efficiency of the photo-Fries rearrangement,
T. Mori, M. Takamoto, H. Saito, T. Furo, T. Wada, and Y. Inoue,
Chem. Lett., 33, 256 (2004).
101. Isolation of cyclohexadienone intermediates in the photo-Fries rearrangement of 2,4-dimethylnaphth-1-yl and 1,4-dimethylnaphth-2-yl 2,4,6-trimethylbenzoates,
Mori, Tadashi; Takamoto, Makoto; Saito, Hideaki; Furo, Takahiro; Wada, Takehiko; Inoue, Yoshihisa,
Chem. Lett., 33, 254 (2004).

2003

100. Bovine Serum Albumin-Mediated Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate,
T. Wada, M. Nishijima, T. Fujisawa, N. Sugahara, T. Mori, A. Nakamura, Y. Inoue,
J. Am. Chem. Soc. 125, 7492 (2003).
99. Solid-Phase Synthesis of Peptide Ribonucleic Acids (PRNA),
T. Wada, H. Sato, Y. Hashimoto, and Y. Inoue,
Tetrahedron, 59, 7871 (2003).
98. Supra-Molecular Self-Assemblies of -Cyclodextrins with Aromatic Tethers: Factors Governing the Helical Columnar versus Linear Channel Super-Structures,
Y. Liu, Z. Fan, H. Zhang, Y. Yang, F. Ding, T. Wada, and Y. Inoue,
J. Org. Chem. 68, 8345 (2003).
97. A Novel Strategy for Reversible Control of Conformation and DNA/RNA Recognition of Peptide Ribonucleic Acid (PRNA) by External Factors,
T. Wada, H. Sato, and Y. Inoue,
Nucleic Acids Research, Suppl., 3, 213(2003).
96. Pressure control of enantiodifferentiating photoisomerization of cyclooctenes sensitized by chiral benzenepolycarboxylates. The origin of discontinuous pressure dependence of the optical yield,
M. Kaneda, A. Nakamura, S. Asaoka, H. Ikeda, T. Wada, and Y. Inoue,
Org. Biomol. Chem., 1, 4435 (2003).
95. Acid-controlled photoreactions of aryl alkanoates: competition of trans-esterification, decarboxylation, Fries-rearrangement and/or transposition,
T. Mori, M. Takamoto, T. Wada, and Y. Inoue,
Photochem. Photobio. Sci, 2, 1187 (2003).
94. Selective Binding of Steroids by 2,2'-Biquinoline-4,4'-dicarboxamide-Bridged Bis(-cyclodextrin): Fluorescence Enhancement by Guest Inclusion,
Y. Liu, Y. Song, H. Wang, H. Zhang, T. Wada, Y. Inoue,
J. Org. Chem. 68, 3687 (2003).
93. Detail CD spectra analysis in view of angular momentum using chiral Eu(III) complexes,
Y. Hasegawa, T. Tomita, Y. Wada, T. Wada, Y. Inoue, S. Yanagida,
Kidorui, 42, 132 (2003).
92. Synthesis of Phosphoryl-Tethered -Cyclodextrins and Their Molecular and Chiral Recognition Thermodynamics,
Liu, Yu; Li, Li; Li, Xiao-Yun; Zhang, Heng-Yi; Wada, Takehiko; Inoue, Yoshihisa,
J. Org. Chem., 68, 3646 (2003).
91. First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by lewis acid cyclization of a resorcinol monoalkyl ether,
M. Klaes, C. Agena, M. Kohler, M. Inoue, T. Wada, Y. Inoue, J. Mattay,
Eur. J. Org. Chem., 1404 (2003).
90. Microenvironmental Polarity Control of Electron-Transfer Photochirogenesis. Enantiodifferentiating Polar Addition of 1,1-Diphenyl-1-alkenes Photosensitized by Saccharide Naphthalenecarboxylates,
S. Asaoka, T. Wada, and Y. Inoue,
J. Am. Chem. Soc., 125, 3008 (2003).
In Chiral Photochemistry; Y. Inoue and V. Ramamurthy, Eds.; Marcel Dekker: New York, 2004.

Prof. Takehiko WADA:

Division of Materials Design, Institute of Multidisciplinary Research for Advanced Materials,
Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai 980-8577, JAPAN

E-mail : hiko@tagen.tohoku.ac.jp
Tel +81-(0)22-217-5608
Fax +81-(0)22-217-5608

HP: http://www.tagen.tohoku.ac.jp/labo/wada/