List of Dissertation Abstract
NameSupervisor（Environment and Natural Sciences

Title
Identification andYoshihiroKazuyuki

ABEHIRATSUKA

Characterization of a SmallMolecule that Induce
Pathogenesis-responsive Gene
Arabidopsis VSP1Life Sciences Course）

Abstract
Plant activators induce systemic acquired resistance and are successfully used for disease control, but
defense gene inducers activating jasmonic acid（JA）signaling pathaways have not been reported so far.
Thereby we have established useful experimental system for investigating novel plant activators
through bioluminescence monitoring fusion gene of Arabidopsis VSP1 gene, which have been
identified as marker gene of JA signaling pathways, and luminescence gene. Using this experimentalsystem, I investigated a novel compound as plant activators candidate.

[4+2] cycloaddition of 2-oxo-

YoshitakaKiyoshi

IKEDA

HONDA

2H-pyrane-4,5-2-oxo-2H-pyrane is oxygen-containing heterocyclic compound and is known as 4π component ofdiethyldicarboxylate with

[4+2] cycloadditions. In this study, I investigated a new and simple method of synthesis of phthalicacetylenes and Synthetic

acid derivatives by [4+2] cycloaddition of 2-oxo-2H-pyrane-4, 5-diethyldicarboxylate with acetylenes.

investigation toward

In addition, isoindolocycloctine derivative for strain-promoted click reaction was prepared by using theisoindolocyclooctynes forpresent [4+2] cycloaddition as a key step.

application to click chemistry.
We developed the gene-expression monitoring system with luciferase reporter fused promoter region
The monitoring of protein
Hirotaka

Kazuyuki

dynamics related to disease

ISHIDAHIRATSUKA

resistance using luciferasefused proteinof a target gene. This system is applied to high-throughput screening for new bioactive compounds.
However, it is difficult to analyze mechanisms of bioactive candidates because this assay only
monitors gene expression indirectly. Here, to investigate mechanisms of candidates, we attempted todevelop a new assay system for monitoring protein dynamics using luciferase-fused protein. As aresult, we succeed in monitoring protein-protein interaction and protein degradation related to disease
resistance.
Intramolecular [2+2]photocycloaddition is an important method in organic synthesis directed toward

Arisa ITO

Selective synthesis of pinanol

target molecules. Bicyclo[3.1.1]heptane skeleton is common structure of bergamotene family which isKiyoshi

derivative via intramolecular

famous for perfume and/or having bioactivity. In this study, regioselective intramolecularHONDA[2+2]photocycloaddition and[2+2]photocycloaddition of 1,6,8-trienes having ester moiety for constructing theapplication to bergamotenes

bicyclo[3.1.1]heptane ring system was achieved. Furthermore, bergamotenoic acid, which is expected
as the agrochemicals, and its derivatives are synthesized by applying this protocol.We report the first data of glycolytic oscillations in individual cancer (HeLa) cells. HeLa cells starved
Relationships between theof glucose or both glucose and serum exhibited glycolytic oscillations in nicotinamide adenine

Yoshihiro

Takashiglycolytic oscillations and thedinucleotide (NADH). We also found that glycolytic oscillations have strong relevance to cellular

ITOH

AMEMIYA

quiescence in cervical cancer

proliferative potential. Our results demonstrate that starved HeLa cells exhibited glycolytic oscillations

HeLa cells

induced by the Crabtree and/or the Warburg effect, and that their strong oscillations ware probably due
to the less use of anabolic pathway.

Carrier Transport Properties ofTakuya

ShinyaUEHARA

MATSUMOTO

Field-Effect Transistors basedon Molecularly-Oriented Thin
Films and Single Crystals of a
Bisazomethine Dye

The carrier transport properties of molecularly-oriented film and single crystal transistors withbisazomethine derivatives were discussed. The enhancement of the carrier mobility was observed in
the molecularly-oriented films. The polarization microscopy revealed that the π- π stacking direction istilted at about 60 degree to the long axis of the needle crystal. The bottom-contact single crystal
transistor showed a hole mobility of 1.1×10-2 cm2 V-1 s-1 which is the highest value observed in thebisazomethine derivatives.
Plants are capable of detoxifying toxic substances through defense genes such as Cytochrome P450

Bioluminescence reporter（CYP）and Glutathione S-transferase（GST）．In this study，I established an experimental system ofYu

Kazuyukisystem to monitor defense gene bioluminescence reporter assay to GST expression in Arabidopsis thaliana transformed by recombinantONOHARAHIRATSUKA

expression in response tovector fused GST promoter and firefly luciferase．Moreover，I investigated a group of compounds

Herbicide Safeners treatment

activating detoxification ability：Herbicide Safeners（HS），and searched candidate compounds of HS
by using its experimental system．

Tatsuya

ShinyaOHASHIMATSUMOTO

Cocrystal of a color developer,

The cocrystals of a fluoran dye and a bisphenol-S derivative 1 for high-performance thermal paper

3,3’-diallyl-4,4’-dihydroxy-were obtained. The structure of the cocrystal was analyzed by X-ray structure analysis and the result

diphenyl sulfone, with ashowed that the hydroxy group of 1 plays an important role in the coloration of the fluoran dye. This

fluoran dye for highcocrystal structure was also found to be thermally stable. Various intermolecular interactions between

performance thermal paper

1 and the dye were suggested to contribute to the stability of the cocrystal structure.
The silver nanoparticle synthesis using tannic acid, green and low cost synthesis is expected, but

YasuhikoTakashiOHARAAMEMIYA

The stoichiometry of the silver

the reaction mechanism is unknown. In this study, we examined the stoichiometric ratio of thisnanoparticles synthesis inreaction using catechol derivatives

catechol derivatives

tannic acid. As a result,we confirmed that both of them reduced 4 or 6 silver ions per molecule and(3,4-dihydroxybenzoic acid and 4-methylcatechol) similar tothe conventional hypothesis is wrong.

Synthesis of 1-pyrazoline

2,2'-spirobiindane has a rigid backbone and is thought to be a promising ligand for metal catalysts withKentoKiyoshi

having C2-symmetrichigh stability. In this study, 1-pyrazoline, azoxy, and azodioxide combounds having a 2,2'-KURAUCHI

HONDA

spirobiindane structure and its

spirobiindane backbone were synthesized for application as a ligand. We found that azodioxide canoxides

accelerate the reaction as a ligand in the N-arylation reaction of benzylamine.
The novel macrocyclic 4’,5’-dioctyl-o-terphenyl oligomers connected by butadiyne linkages consider
to be rigid π conjugated molecules with large inner cavities. 4’,5’-Dioctyl-4,4”-diethynyl-o-terphenyl

Synthesis and properties ofIkumi SAKO

Hiroyukigiant macrocyclic 4’,5’-OTANI

dioctyl-4,4”-diethynyl-oterphenyl oligomers

was synthesized as the corresponding precursor of these macrocycle oligomers. The cyclic oligomersof 4’,5’-dioctyl-4,4”-diethynyl-o-terphenyl, such as dimer, trimer, hexamer, octamer, and decamer,
were synthesized by using copper(II) acetate-mediated Eglinton coupling reaction of the precursor in
pyridine or pyridine-methanol. Although the cyclic dimer and the cyclic trimer were formed as major
products under high dilution conditions, giant cyclic oligomers such as hexamer, octamer, and decamer
were obtained under standard conditions. The reaction mechanism for the formation of thesemacrocycle oligomers and their optical properties were discussed in detail.
The structure, optical properties, and complexation behavior of 1,8-diphenyl-10-mesitylanthracene
cyclic dimer with a rigid [5,5]biphenylophane frame was investigated. The optical properties of thedimer were characterized by the UV-vis and FL spectra in solution and in the solid state. Since theHiroto SANO

Hiroyuki

Synthesis and Properties ofcyclic dimer has a suitable inner cavity for including a small cation, it showed complexation behavior

OTANI

novel π conjugated oligomers

with Cu(I) cation and Ag(I) cation. In addition, a cyclic p conjugated oligomer in which benzene andnaphthalene are alternately linked at the ortho position are expected to show unique physicalproperties. The cyclic p conjugated oligomer was synthesized by using by using Lewis acid-catalyzed
benzannulation via [4+2] cycloaddition of o-alkynyl(oxo)benzene with tribenzodehydro[12]annulene.
Multifunctional p-expanded macrocyclic oligothiophenes are a molecule having interesting structure,
unique optical behavior, and polymorphism. I have synthesized p-expanded macrocyclic oligo-3,4-Synthesis, Structure anddiphenylthiophene 8-mer and 6-mer using McMurry coupling reaction of corresponding dialdehyde

Yoshihiro

Hiroyuki

Properties ofprecursors. The macrocyclic oligothiophene 8-mer existed as a mixture of isomers, E / E and Z / Z andSUZUKI

OTANI

p-Expanded Cyclic Oligo-3,4-the isomers shown mutual photoisomerization, and differed in optical properties due to thediphenylthiophenes

photoisomerization. The macrocyclic 6-mer formed polymorphs such as single crystals, fibers, needles,and rods. Furthermore, the yellow fibers of this 6-mer showed vapochromism with vapor-induced
quasi-reversible shape change, and the vapor-induced color change was repeated more than 10 times.

Tropolone is the typical example of non-benzenoid compound which possess pronounced aromaticcharacter. The synthesis, structure, and optical properties of two 5-(4-N,N-diarylaminophenyl)
tropolones extended by acetylene bond, as the novel tlan type D-p-A chromophoric tropolone
TakutoHiroyukiNAKAMURA OTANI

Synthesis and Properties of 5Arylethyniltropolones

molecules, were investigated. Both 5-(4-N,N-diphenylaminophenyl)ethynyltropolone and 5-(4-N,Ndianisylaminophenyl)ethynyltropolone were obtained by a synthetic route with Sonogashira crosscoupling reaction as a key step. The optical properties of the tlan type D-p-A tropolone molecules werecharacterized by the UV-Vis and fluorescence spectra in solution. I have discussed the opticalproperties of 4-N,N-diphenylamino phenyl derivative and 4-N,N-dianisylaminophenyl derivative insolution.
DNA double strand break (DSB) has been known as severe damage for the genetic information and theShinya
NanaumiAnalysis of transcription
Shinichi Ogata

control region of AtRad51
gene

mechanisms of DSB repair have long been investigated in varieties of species. The promoter region ofAtRad51 gene was analyzed in detail and the existence of element(s) responding to DSB will bediscussed. The analysis of the 5’ region of AtRad51 gene promoter strongly suggested that theexistence of the DNA elements that respond to DSB stimuli. We will analyze these elements in detailand determine the transcription factor(s) that bind to the DSB response elements near future.
I studied the optical properties of pyrazine derivatives having benzyl groups substituted by a halogen atom

Optical properties of 2,5Risa

Shinyadiamino-3,6-dicyanopyrazine

HIROSAWA

MATSUMOTO

dyes having mono-substituted
benzyl substituentsor a methyl group in the para- or ortho- position. All derivatives showed similar optical properties inchloroform solution. However, in solid states, the absorption characteristics and maximum fluorescencedepended on the geometries of amino groups in a crystalline state. The amino geometries in the red crystalforms adopted sp2-like configuration, while the amino geometries adopted sp3-like configuration in theyellow crystal forms. The studied crystal forms exhibited a variety of fluorescence quantum yields
depending on the species and positions of the terminal substituent.

Optical properties ofpolymorphs ofTakeruShinyadiketopyrrolopyrrole

FUJISHIMA

MATSUMOTO

derivatives having propyl andbutyl substituents on aminogroups

The absorption and fluorescence properties of two polymorphs of N,N'-dipropylated and N,N'dibutylated diketopyrrolopyrrole derivatives were studied to investigate the relationship between
crystal structure and optical properties. Their absorption properties were found to be influenced bymolecular structure in the crystalline state. On the other hand, their fluorescence properties weresuggested to be correlated with the stacking structure of the dye molecules in the crystals.

Lichen compounds which are the secondary metabolites of lichens are effective means foridentification and characterization of lichens. It is known that the lichen compounds of Stereocaulon
Naoki

TakashiFUJIMOTOAMEMIYA

Evaluation of the effect ofsorediiferum emit strong fluorescence under UV irradiation. Evaluation of copper contamination bycopper contamination on lichen fluorescence measurement becomes possible if the lichen compounds change concentration according
compounds

to copper contamination. In this study, the larger copper concentration, the lower the fluorescenceintensity. A research result was obtained as the first step of the environmental contamination evaluation
method utilizing fluorescence from lichens.

Marina MUTO

Kiyoshi HONDA

Stereoselective construction ofSynthesis of terpene compounds which have been used as aroma chemicals and medicines, is one oftrisubstituted olefins using

significant issues. Especially stereoselective construction of trisubstituted olefin units is importantcondensation/aza-Claiseninterest on the preparation of terpene compounds. [3,3]-Rearrangement reaction is one of the reaction

rearrangement reaction ofwhich is used for synthesis of terpene compounds frequently. In this study, I examined the preparation

allylamines with carbonylof trisubstituted olefins via generation of enammonium salts from allylamines with carbonylcompounds

compounds, followed by aza-Claisen rearrangement.
The indane-based skeleton is one of the basic skeletons commonly found in natural substances having
a variety of physiological activities.It has also been reported that the polysubstituted indane derivatives

Qixiao QIKiyoshi HONDA

Stereoselective Synthesis of

is used as an asymmetric catalyst in recent years.Therefore, a novel synthetic method ofPolysubstituted Indane

polysubstituted indane derivatives is desired.Herein, we would like to describe the stereoselectiveDerivatives

synthesis of polysubstituted indane derivatives via a new intramolecular skeletal transformation from
7-azabenzonorbornadienes in the presence of an acid- catalyst.
.