Faculty Profiles - TANAKA Kentaro

Papers - TANAKA Kentaro

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Synthesis and Structure-Activity Relationships of Nonnatural β-C-Nucleoside Triphosphates Bearing an Aromatic Nucleobase with Phenolic Hydroxyl Groups: Inhibitory Activities against DNA Polymerases Reviewed

S. Aketani, K. Tanaka, K. Yamamoto, A. Ishihama, H. Cao, A. Tengeiji, S. Hiraoka, M. Shiro, and M. Shionoya

J. Med. Chem. Vol. 25 page： 5594-5603 2002

Spontaneously resolved chiral interpenetrating 3-D nets with two different zinc coordination polymers [7]

M. Sasa, K. Tanaka, X. H. Bu, M. Shiro, M. Shionoya

Journal of the American Chemical Society Vol. 123 page： 10750-10751 2001.10

Nickel-mediated alcoholysis reaction of carbon-nitrogen triple bond: Structural characterization of an unprecedented moisture stable imido ester with an E-configuration

Xian He Bu, Miao Du, Kentaro Tanaka, Mitsuhiko Shionoya, Motoo Shiro

Inorganic Chemistry Communications Vol. 4 page： 150-152 2001.4

Novel organic crystals as candidates for frequency up-converted materials: Syntheses and crystal structures of two Tröger's bases

X. H. Bu, M. Du, L. J. Zhao, K. Tanaka, M. Shionoya, M. Shiro

Journal of Chemical Research - Part S page： 243-245 2001.1

Spontaneously Resolved Chiral Interpenetrating 3-D Nets with Two Different Zinc Coordination Polymers Reviewed

M. Sasa, K. Tanaka, M. Shiro, X.-H. Bu, and M. Shionoya

J. Am. Chem. Soc. Vol. 123 page： 10750-10751 2001

A Palladium-Mediated DNA Base Pair of a beta-C-Nucleoside Possessing a 2-Aminophenol as the Nucleobase Reviewed

M. Tasaka, K. Tanaka, M. Shiro, and M. Shionoya

Supramol. Chem. Vol. 13 page： 671-675 2001

An approach to metal-assisted DNA base pairing: Novel β-C-nucleosides with a 2-aminophenol or a catechol as the nucleobase International journal

Kentaro Tanaka, Motoyuki Tasaka, Honghua Cao, Mitsuhiko Shionoya

European Journal of Pharmaceutical Sciences Vol. 13 ( 1 ) page： 77 - 83 2001

Language：English Publishing type：Research paper (scientific journal)

The metal-chelating β-C-nucleoside having a phenylenediamine moiety as the nucleobase was previously found to form a stable 2:1 complex with a Pd2+ ion in aqueous media, where hydrogen bonding is replaced by metal coordination in the base pairing, thereby creating a novel hybridization motif in duplex DNA. In this regard, we have further designed two types of artificial β-C-nucleosides possessing a metal-chelating site (a 2-aminophenol or a catechol) as the nucleobase moiety. These artificial nucleosides are directed toward controlling the net charges of the metal-assisted base pairs. This paper describes convenient syntheses of the artificial nucleosides bearing a 2-aminophenol or a catechol moiety. Each nucleoside was directly synthesized through 2′-deoxy derivative via a Friedel-Crafts coupling reaction as the key step between the aromatic ring and ribose moiety, whereas the nucleoside having a phenylenediamine moiety was prepared in rather longer steps through an RNA type intermediate followed by the removal of 2′-hydroxyl group. © 2001 Elsevier Science B.V.

DOI： 10.1016/S0928-0987(00)00210-4

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PubMed

A novel polymeric Ag(I) complex consisting of two three-dimensional networks which are enantiometric and interpenetrating

X. H. Bu, K. Biradha, T. Yamaguchi, M. Nishimura, T. Ito, K. Tanaka, M. Shionoya

Chemical Communications page： 1953-1954 2000.10

Synthetic incorporation of metal complexes into nucleic acids and peptides directed toward functionalized molecules

M. Shionoya, K. Tanaka

Bulletin of the Chemical Society of Japan Vol. 73 page： 1945-1954 2000.9

Publishing type：Research paper (scientific journal)

Novel synthetic approaches for incorporation of metal complexes into nucleic acids and peptides are described. First, novel artificial β-C-nucleosides bearing a chelator nucleobase (2-aminophenol, catechol, or o-phenylenediamine) have been synthesized. These artificial nucleobases were introduced for alternative base pairing through metal coordination instead of the hydrogen bonding in natural DNA.1HNMR and mass spectral studies clearly showed that o-phenylenediamine-type nucleoside forms a stable 2: 1 square-planar complex with a Pd(II) ion, providing an alternative DNA base pairing through metal complexation. Secondly, an efficient strategy for the liquid-phase synthesis of cyclic metallopeptides having a repeating Gly-L-Cys(terpyPt(II)) sequence, cyclo[-Gly-L-Cys(terpyPt(II))-](n)Cl(n) (n = 3, 4), has been developed. These cyclic metallopeptides were obtained by cyclization of the corresponding linear peptides, H2[-Gly-L-Cys(terpyPt(II))-](n)OH-(CF3CO2)(n+1) (n = 3, 4), in moderate yields. The former cyclic hexapeptide was found to act as a positively charged anion receptor. This synthetic approach would provide a powerful tool for arraying metal centers on cyclopeptide frameworks.

DOI： 10.1246/bcsj.73.1945

Scopus

A spontaneously resolved chiral molecular box: A cyclic tetranuclear Zn(II) complex with DPTZ (DPTZ = 3,6-di-2-pyridyl-1,2,4,5-tetrazine)

Xian He Bu, Xian He Bu, Xian He Bu, Hiromasa Morishita, Kentaro Tanaka, Kumar Biradha, Sanae Furusho, Mitsuhiko Shionoya

Chemical Communications page： 971-972 2000.6

An alternative base-pairing of catechol-bearing nucleosides by borate formation

Honghua Cao, Kentaro Tanaka, Mitsuhiko Shionoya

Chemical and Pharmaceutical Bulletin Vol. 48 page： 1745-1748 2000.1

Publishing type：Research paper (scientific journal)

A chelator-type β-C-nucteoside having a catechol ligand as the nucleobase was found to form a stable 2 : 1 complex with trimethyl borate, which was characterized by1H-NMR and etectrospray ionization time-of-flight (ESI-TOF) mass speetroseopies. Both phosphoramidite and phosphotriester derivatives of this nueleoside were also prepared as synthetic precursors for DNA oligomer syntheses.

DOI： 10.1248/cpb.48.1745

Scopus

PubMed

Self-assembly of chelator-type nucleic acid mimics into a single-stranded Zn^IIcoordination polymer

Akihiko Hatano, Kentaro Tanaka, Motoo Shiro, Mitsuhiko Shionoya

Chemistry Letters page： 822-823 2000.1

Publishing type：Research paper (scientific journal)

The synthesis of a "chelator-type" adenine mimic, which has two metal binding sites, and its ZnII-assisted self-assembly into a single-stranded coordination polymer are described. The UV absorption changes of a 1 : 1 mixture of the ZnIIcomplex and a single-stranded DNA oligomer (dT)70showed the temperature-dependent hyperchromic effect in an analogous manner as thermal denaturation processes of natural DNA duplexes.

DOI： 10.1246/cl.2000.822

Scopus

Cyclic metallopeptides, cyclo[Gly-L-Cys(terpyPt(II))](n)Cl(n)

Kentaro Tanaka, Kentaro Tanaka, Kazuki Shigemori, Mitsuhiko Shionoya, Mitsuhiko Shionoya

Chemical Communications page： 2475-2476 1999.12

Synthesis of a novel nucleoside for alternative DNA base pairing through metal complexation

Kentaro Tanaka, Mitsuhiko Shionoya, Mitsuhiko Shionoya

Journal of Organic Chemistry Vol. 64 page： 5002-5003 1999.7

Artificial DNAs with metal-assisted base pairs.

K. Tanaka, H. Cao, M. Tasaka, M. Shionoya

Nucleic acids symposium series page： 111-112 1999.1

Anisotropic electric conductivity in an aligned DNA cast film

Y. Okahata, T. Kobayashi, K. Tanaka, M. Shimomura

Journal of the American Chemical Society Vol. 120 page： 6165-6166 1998.1

DNA-aligned cast film and its anisotropic electron conductivity International journal

Y. Okahata, T. Kobayashi, H. Nakayama, K. Tanaka

Supramolecular Science Vol. 5 ( 3-4 ) page： 317 - 320 1998

Language：English Publishing type：Research paper (scientific journal) Publisher：Elsevier Sci Ltd

A DNA-lipid cast film was prepared, in which counter cations of DNA phosphates were replaced by cationic amphiphiles. The film is transparent, physically strong, and water-insoluble. DNA strands could be aligned in one direction by stretching the film. The aligned-DNA film showed a large anisotropic and ohmic electric current (10-5 S cm-1, A⊥/A = 104) along DNA strands in the film.

DOI： 10.1016/S0968-5677(98)00025-X

Scopus

Oriented thin films of a DNA-lipid complex

Yoshio Okahata, Kentaro Tanaka

Thin Solid Films Vol. 284-285 page： 6-8 1996.9

Publishing type：Research paper (scientific journal)

Organic thin films in which DNA double strands aligned in one direction were prepared by two methods: 1) polyion complexes of DNA anions and cationic amphiphiles was prepared and the organic solution of the DNA-lipid complex was cast and the obtained transparent film was stretched in one direction, and 2) DNA anions were solubilized in subphase with intercalated dyes and were transferred with cationic lipid monolayers by vertical dipping method. DNA strands could be aligned along stretching direction in the cast film and along dipping direction in the LB film. The orientation of DNA strands in the thin films were confirmed by X-ray diffraction and polarized absorption spectra.

DOI： 10.1016/S0040-6090(96)08830-X

Scopus

Orientation of DNA double strands in a Langmuir-Blodgett film

Yoshio Okahata, Takuya Kobayashi, Kentaro Tanaka

Langmuir Vol. 12 page： 1326-1330 1996.3

Publishing type：Research paper (scientific journal)

A cationic amphiphile monolayer was spread on a subphase containing DNA double strands and intercalating dyes, and the polyion complex DNA/dye/cationic monolayer was transferred to a substrate by the vertical dipping method. It was confirmed by X-ray diffraction patterns and polarized absorption spectra that the dye-intercalated DNA strands were aligned along the dipping direction in the LB film. DNA strands are not aligned in the LB film without intercalating dye molecules. When the DNA-lipid monolayers were deposited by a horizontal lifting method instead of a vertical dipping method, DNA strands were randomly oriented in the film. The orientation of DNAs was decreased when the monolayer packing was decreased by using a low surface pressure or an expanded monolayer. Thus, the rigid, dye-intercalated DNA strands could be oriented during the vertical dipping process.

Scopus

A DNA-lipid complex in organic media and formation of an aligned cast film

K. Tanaka, Y. Okahata

Journal of the American Chemical Society Vol. 118 page： 10679-10683 1996.1

Publishing type：Research paper (scientific journal)

A novel DNA-lipid complex is prepared by replacing sodium counter cations by cationic amphiphilic lipids (1). The DNA-lipid complex is insoluble in aqueous solutions, but is soluble in most orgamc media such as benzene, ethanol, and chloroform. The DNA-lipid complex was confirmed to form double helical strands even in organic media, and the internal conformation of DNA strands could be reversibly changed from B-form to C-form in the organic solution (CHCl3/EtOH = 4:1) by changing the water content. A self-standing, water-insoluble DNA-lipid (1) film was prepared by casting from the organic solution and could be stretched to produce oriented DNA strands with their axes aligned along the stretching direction. The film can be impregnated with the drug ethidium bromide in the aqueous solution. The linear dichroism characteristics of the drug-DNA film show that the DNA strands are well oriented and the ethidium molecules are intercalated, as they are in normal aqueous solutions.

DOI： 10.1021/ja9617855

Scopus

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Papers - TANAKA Kentaro