Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Volume 79 , Issue 2
Showing 1-23 articles out of 23 articles from the selected issue
Award Accounts
The Chemical Society of Japan Award for 2004
  • Shunichi Fukuzumi
    2006 Volume 79 Issue 2 Pages 177-195
    Published: 2006
    Released: February 10, 2006
    JOURNALS FREE ACCESS
    Bioinspired electron-transfer systems including artificial photosynthesis and respiration are presented herein together with some of their applications. First, multi-step electron-transfer systems composed of electron donor–acceptor ensembles have been developed, mimicking functions of the photosynthetic reaction center. However, a significant amount of energy is lost during the multi-step electron-transfer processes. Then, as an alternative to conventional charge-separation functional molecular models based on multi-step long-range electron transfer within redox cascades, simple donor–acceptor dyads have been developed to attain a long-lived and high energy charge-separated state without significant loss of excitation energy, by fine control of the redox potentials and of the geometry of donor–acceptor dyads that have small reorganization energies of electron transfer. Such simple molecular dyads, capable of fast charge separation but extremely slow charge recombination, have significant advantages with regard to synthetic feasibility, providing a variety of applications including construction of organic solar cells and development of efficient photocatalytic systems for the solar energy conversion. An efficient four-electron reduction of dioxygen to water by one-electron reductants such as ferrocene derivatives as well as by an NADH analog has also been achieved as a respiration model by using a cofacial dicobalt porphyrin that can form the μ-peroxo Co(III)–O2–Co(III) complex. The catalytic mechanism of the four-electron reduction of dioxygen has been clarified based on the detailed kinetic study and the detection of the intermediate.
The Chemical Society of Japan Award for Creative Work for 2003
  • Hirohiko Kono, Yukio Sato, Manabu Kanno, Katsunori Nakai, Tsuyoshi Kat ...
    2006 Volume 79 Issue 2 Pages 196-227
    Published: 2006
    Released: February 10, 2006
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    We have developed a method for describing the reaction dynamics of a polyatomic molecule in intense laser fields. First, the dynamical behavior of H2+ and H2 in near-infrared, intense laser fields (I > 1013 W cm−2 and λ > 700 nm) was examined; accurate evaluation of the electronic and nuclear wave packet was achieved by the dual transformation method that we developed. Using “field-following” time-dependent adiabatic states defined as eigenfunctions of the “instantaneous” electronic Hamiltonian, we have clarified the dynamics of bound electrons, ionization processes, Coulomb explosion processes, and molecular vibrations of H2+ and H2. The analyses indicate that the multielectron dynamics and nuclear dynamics of polyatomic molecules in intense fields can be described by using the potential surfaces of time-dependent adiabatic states and the nonadiabatic coupling elements between those states. To obtain time-dependent adiabatic states of a molecule, one can diagonalize the electronic Hamiltonian including the interaction with the instantaneous laser electric field by ab initio molecular orbital (MO) methods. The time-dependent adiabatic potentials obtained are used to evaluate the multichannel nuclear dynamics until the next ionization process. We have applied the time-dependent adiabatic state approach to reveal the characteristic features of the dynamics of structural deformations of CO2 and its cations in a near-infrared intense laser field. The experimentally observed stretched and bent structure of CO23+ just before Coulomb explosions originates from the structural deformation of CO22+. We also revealed the mechanism of the experimentally observed bond dissociation of C2H5OH; we found that the relative probability of C–O bond cleavage to that of C–C bond cleavage becomes smaller with decreases in the pulse length. This example clearly shows that field-induced nonadiabatic transitions play a decisive role in the reaction dynamics of molecules in an intense laser field.
BCSJ Award Article
  • Yasuo Kameda, Motoya Sasaki, Yuko Amo, Takeshi Usuki
    2006 Volume 79 Issue 2 Pages 228-236
    Published: 2006
    Released: February 10, 2006
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    Neutron diffraction measurements have been carried out at 25 °C for aqueous 18 mol % lithium alaninate heavy water solutions, [C*H3C*H(*ND2)COO*Li]0.18(D2O)0.82, in which the isotopic compositions 14N/15N, HM/DM (HM: methyl-hydrogen atom), and HM′/DM′ (HM′: methine-hydrogen atom) within the alaninate ion, and 6Li/7Li for the lithium ion were changed. The hydration structures of both alaninate and lithium ions were derived from the least squares fitting analysis of observed first-order difference functions, ΔN(Q), ΔHM(Q), ΔHM′(Q), and ΔLi(Q). It was revealed that the amino group of the alaninate ion forms a hydrogen bond of the N···Dw1–OwDw2 type (Ow and Dw denote water–oxygen and water–deuterium atoms, respectively) with ca. one D2O molecule (rNDw1 = 2.00(1) Å, ∠N···Dw1–Ow = 165(10)°), and simultaneously forms hydrogen bonds of the N···OD2 type with 1.4(1) D2O molecules (rNO = 2.95(5) Å, rND = 3.35(5) Å). The numbers of water molecules neighboring hydrogen atoms within the methyl- and methine-group of the alaninate ion were determined to be 0.62(1) and 0.86(9), respectively. The first coordination shell of Li+ was found to consist of 2.42(5) D2O molecules and 2.3(2) alaninate ions. The bond angle ∠Li+···Oc–C (Oc: carboxyl-oxygen atom) and the dihedral angle between the plane involving atoms Li+···Oc–C and the plane of the carboxyl group of the alaninate ion were determined to be 101(1) and 74(1)°, respectively.
Articles
  • Takahiro Ueda, Hironori Omi, Takanori Yukioka, Taro Eguchi
    2006 Volume 79 Issue 2 Pages 237-246
    Published: 2006
    Released: February 10, 2006
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    The pressure dependence of a 129Xe chemical shift (δ) and the local density of xenon adsorbed in activated carbon fiber (ACF) with slit-pore widths of 0.7–1.1 nm was investigated using in-situ high-pressure 129Xe NMR. 129Xe chemical shift values below 0.025 MPa change linearly with equilibrium pressure. The initial slope of the pressure dependence of δ led to a shift value at zero pressure, δS′, which approximately reflects the xenon–wall interaction. A statistical model incorporating the xenon–wall interaction well interprets the dependence of δS′ on the pore width. Furthermore, in a higher-pressure region, the density dependence of the chemical shift led to the xenon–xenon interaction via the virial coefficients of the chemical shift up to the second order on density (the third-virial coefficient). The second-virial coefficient (a coefficient for the linear term of density) depended on the pore width. Increasing the slit width from 0.7 to 1.1 nm increased the second-virial coefficient, δ1, from 42 × 10−3 to 78 × 10−3 ppm kg−1 m3, suggesting that the space accessible by the surrounding xenon atoms increases when the slit width increases. This aspect reveals the size effect of the xenon–xenon interaction in nanospace.
  • Xiaoli Hu, Shaopu Liu, Zhongfang Liu
    2006 Volume 79 Issue 2 Pages 247-251
    Published: 2006
    Released: February 10, 2006
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    A flow injection analysis (FIA) method coupled with resonance Rayleigh scattering (RRS) detection for the determination of kanamycin sulfate (KANA) was developed. The method is based on the ion-association reaction of KANA with acid triphenylmethane dyes such as aniline blue W. S (AB) and methyl blue (MB) by virtue of electrostatic and hydrophobic interaction forces, which results in a significant enhancement of RRS intensity; their maximum scattering peaks are all at 346 nm. The optimum conditions of the reactions and the flow-through parameters including the length of reaction tubing, the flow rate of the carrier stream and the sample injection volume are discussed in this paper. Under the optimum experimental conditions, the linear ranges for both systems are 0.02–12.0 μg mL−1. The detection limits (3σ) are 4.2 ng mL−1 for the AB system and 5.0 ng mL−1 for the MB system and the relative standard deviation for 9 replicate measurements of 2.0 μg mL−1 KANA solution was 1.1%. The proposed method was successfully applied to the determination of KANA in commercial KANA injection, urine and serum samples, and the sample throughput was 30 h−1.
  • Masahito Kodera, Motoharu Itoh, Koji Kano, Takuzo Funabiki
    2006 Volume 79 Issue 2 Pages 252-261
    Published: 2006
    Released: February 10, 2006
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    The peroxodiiron(III) complexes [Fe2(O)(O2)(OAc)(hexpy)](CF3SO3) (2) and [Fe2(O)(O2)(OAc)(tripy)2](ClO4) (4) (hexpy = 1,2-di[6-bis(2-pyridyl)methyl-2-pyridyl]ethane and tripy = 2-di(2-pyridyl)methyl-6-methylpyridine) were prepared by addition of H2O2 to the di(μ-acetato)-μ-oxodiiron(III) complexes [Fe2(O)(OAc)2(hexpy)](CF3SO3)2 (1c) and [Fe2(O)(OAc)2(tripy)2](ClO4)2 (3) in MeCN, respectively. The peroxo complex 2 was isolated as a purple solid, but 4 could not be due to its instability. Detailed spectral studies of 2 and 4 revealed the unique triply bridged μ-acetato-μ-oxo-μ-1,2-peroxodiiron(III) core structures. The spontaneous decomposition of 2 and 4 in various solvent systems was kinetically investigated. The half-life of 2 and 4 in dry MeCN was 8.7 h at 300 K and 10 min at 263 K, respectively, clearly showing that the thermal stability of 2 is markedly enhanced by the hexpy ligand.
  • Aki Hayashi, Yui Nakabayashi, Junko Yasutomi, Hirokazu Nakayama, Mitsu ...
    2006 Volume 79 Issue 2 Pages 262-269
    Published: 2006
    Released: February 10, 2006
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    Glucosamine was directly intercalated into γ-zirconium phosphate (γ-ZrP). The intercalation compound with a monolayer structure was obtained by the interaction between the 2-amino group of glucopyranose and the phosphate group in γ-ZrP. The uptake amount depended on the concentration of the glucosamine aqueous solution rather than reaction time, and reached 0.9 mmol per gram of γ-ZrP at the maximum. On the other hand, chitosan, polysaccharide of glucosamine, could be intercalated into alkylamine-intercalated γ-ZrP as the host compound. Chitosan-intercalated γ-ZrP showed two phases with different interlayer distances. It was confirmed from 13C CP/MAS NMR spectra that chitosan exists in the interlayer region of γ-ZrP for both phases.
  • Yuanguang Zhang, Yi Liu, Shengquan Fu, Fan Guo, Yitai Qian
    2006 Volume 79 Issue 2 Pages 270-275
    Published: 2006
    Released: February 10, 2006
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    Rod-like MnPO4·H2O single crystallites were hydrothermally prepared by the reaction of Mn(NO3)2 with H3PO4 at 130 °C for 16 h. The products were characterized by X-ray powder diffraction (XRD), transmission electron microscopy (TEM), infrared spectrum (IR), and their magnetic properties were evaluated on a vibrating sample magnetometer (VSM). The synthesized single-crystal rods have diameters of 0.1–0.66 μm and lengths of up to several micrometers. The influences of different phosphates, the volume ratio between reaction materials, reaction temperature, and reaction time on the morphology and phase of the final products under hydrothermal conditions are discussed. A possible formation mechanism has been proposed on the growth of MnPO4·H2O single-crystal rods.
  • Abdolraouf Samadi-Maybodi, Nasser Goudarzi, Hossein Naderi-Manesh
    2006 Volume 79 Issue 2 Pages 276-281
    Published: 2006
    Released: February 10, 2006
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    Alkaline solutions containing both silicate and aluminate ions are of considerable research interest inter alia because of their involvement in the synthesis of zeolites. 27Al NMR spectra of alkaline aluminosilicate solutions generally show a maximum of five broad bands. In the present work, we use 27Al NMR to characterize aluminosilicate solutions with different Al/Si ratios using 2-hydroxyethyl(trimethyl)ammonium as a cation template, no alkaline metals are used for preparation of aluminosilicate solutions. To understand the reaction between silicate and aluminate ions in this system, the evolutions of 27Al NMR spectra with time are investigated.
  • Yuji Soneta, Kazuo Miyamura
    2006 Volume 79 Issue 2 Pages 282-287
    Published: 2006
    Released: February 10, 2006
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    A series of [Ni(dmit)2] (dmit = 2-thioxo-1,3-dithiole-4,5-dithiolato) salts of 3,7-bis(dialkylamino)phenothiazin-5-ium (alkyl = methyl (C1S), ethyl (C2S), propyl (C3S), and butyl (C4S)) together with those of 3,7-bis(diallylamino)phenothiazin-5-ium (AS) and 3,7-bis(diethylamino)phenoxazin-5-ium (C2O) have been prepared and analyzed by X-ray crystal structural analysis and diffuse reflectance spectra. All complex salts formed stacking columns containing cations and anions. In the crystal structure of (C1S)[Ni(dmit)2], both C1S cations and [Ni(dmit)2] anions were found to form stacked dimers, and these dimers piled up alternately in columns. In the cases of (C2S)[Ni(dmit)2], (AS)[Ni(dmit)2], and (C2O)[Ni(dmit)2], cations and anions piled up alternately in the form of monomers. In the cases of (C3S)[Ni(dmit)2] and (C4S)[Ni(dmit)2], one anion was sandwiched between two cation dimers to form columns, and another anion layed between these columns. An absorption band appeared at 516–566 nm in the diffuse reflectance spectra, which originated from the absorption of blue cationic dyes, exhibited a large shift by the intermolecular interaction of cation–cation and cation–anion π-stacking. Compounds of (C1S)[Ni(dmit)2] and (C2O)[Ni(dmit)2] were found to behave as semiconductors, exhibiting room temperature conductivities of 3.8 × 10−6 and 4.5 × 10−7 S cm−1, respectively.
  • Toshiaki Tsukuda, Ayaka Nakamura, Takashi Arai, Taro Tsubomura
    2006 Volume 79 Issue 2 Pages 288-290
    Published: 2006
    Released: February 10, 2006
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    Mixed-ligand dinuclear Cu(I) complexes containing both diimine and diphosphine ligands have demonstrated interesting photophyisical properties; the complexes are emissive in solution at room temperature, even with 1,10-phenanthroline (phen) lacking a 2,9-substituted group.
  • Jujie Ren, Junichi Nakashima, Toshio Nakamura
    2006 Volume 79 Issue 2 Pages 291-293
    Published: 2006
    Released: February 10, 2006
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    A Benzo-15-crown-5 modified poly(acrylamide) membrane coated platinum electrode is successfully used to determine the solubility product of CH3COONa in propylene carbonate. The standard Gibbs energies of Na+ and CH3COO transfer from water to propylene carbonate are obtained. The datum of CH3COO is reported for the first time.
  • Susumu Kohata, Yuko Hamabe, Kouki Jyodoi, Masahiko Kurihara, Tomikatsu ...
    2006 Volume 79 Issue 2 Pages 294-296
    Published: 2006
    Released: February 10, 2006
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    Heptakis(2,6-di-O-methyl)-β-cyclodextrin (DM-β-CD), prepared by dissolution in either pure water or acetone and dried at 40 °C, showed a characteristic exothermic change in the range 160–185 °C. Simultaneous X-ray diffractometry and differential scanning calorimetry (XRD-DSC) clearly showed the transition of DM-β-CD from an amorphous to a crystalline state during exothermic reactions.
  • Noriyuki Matsuura, Tatsuya Kawamoto, Takumi Konno
    2006 Volume 79 Issue 2 Pages 297-299
    Published: 2006
    Released: February 10, 2006
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    A diruthenium(II) complex, ΔΔ/ΛΛ-[{Ru(bpy)2}2(μ-L)2]2+ (ΔΔ/ΛΛ-[2]2+), in which two cis-[Ru(bpy)2]2+ units are bridged by two S atoms from two 2-benzoylaminoethanethiolate (L) ligands, was synthesized by the reaction of ΔΔ/ΛΛ-[{Ru(bpy)2}2(μ-Haet)2]4+ (aet = 2-aminoethanethiolate; ΔΔ/ΛΛ-[1]4+) with benzoyl chloride in the presence of a base. The molecular structure and electrochemical properties of ΔΔ/ΛΛ-[2]2+ were discussed in comparison with those of ΔΔ/ΛΛ-[1]4+.
  • Hajime Nagano, Yukiko Iwazaki, Xun Gong, Yuemao Shen, Chiaki Kuroda, R ...
    2006 Volume 79 Issue 2 Pages 300-304
    Published: 2006
    Released: February 10, 2006
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    Intra-specific diversity of Ligularia pleurocaulis was examined from both chemical and genetic aspects, using furanoeremophilanes as the chemical index and the nucleotide sequences in the atpB-rbcL and the ITS1 regions as the genetic index. Four samples of L. pleurocaulis were collected in northwestern Yunnan, and six in southwestern Sichuan. From the ethanol extracts of the roots of all of the samples, four compounds, 6β-angeloyloxy- and 6β-tigloyloxy-furanoeremophil-1(10)-enes, and 6β-angeloyloxy- and 6β-tigloyloxy-furanoeremophil-1(10)-en-3β-ols were isolated. Further, 3β-angeloyloxyfuranoeremophil-1(10)-en-6β-ol and furanoligularenone were isolated from the Yunnan and the Sichuan samples, respectively. Two variants were found for the atpB-rbcL sequence. Base multiplicity in the ITS1 region was observed at only a few positions in the Yunnan samples, whereas it was observed at about 10 positions for the Sichuan samples. These results show that L. pleurocaulis is diverse, both chemically and genetically, and that plants in northwestern Yunnan and those in southwestern Sichuan can be distinguished by their chemical and genetic indexes.
  • Asuka Ohshima, Atsuya Momotake, Tatsuo Arai
    2006 Volume 79 Issue 2 Pages 305-311
    Published: 2006
    Released: February 10, 2006
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    Substituent effects on the ground-state properties of seven naphthalene analogues of salicylideneaniline (17) were studied by comparison of both steady-state and transient absorption spectra. The naphthalene-based salicylideneanilines 15 were prepared from 2-hydroxy-1-naphthaldehyde and corresponding amines. The UV absorption spectra of 15 were largely dependent on the substituent group on the amino group. Transient absorption studies revealed that the introduced naphthyl group in 15 prolonged the lifetime of 1Ktrans in non-polar solvent probably due to the formation of intramolecular hydrogen bonding between nitrogen and C–H hydrogen on the naphthyl group. In acetonitrile, the lifetimes of 16 are much longer than those in benzene, probably because the zwitterionic forms are stabilized in polar solvents, whereas the much shorter lifetime in ethanol suggests that 1Ktrans undergoes the solvent assisted re-enolizaiton reaction in ethanol.
  • Kiyohiko Kawai, Takumi Kimura, Hiroko Yoshida, Akira Sugimoto, Sachiko ...
    2006 Volume 79 Issue 2 Pages 312-316
    Published: 2006
    Released: February 10, 2006
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    To arrange pyrene at the minor groove of DNA, we synthesized a nucleoside derivative possessing a pyrene group on guanine N2. Doubly pyrene-modified duplex DNA was synthesized and the formation rates of the pyrene dimer radical cation were measured upon one-electron oxidation during pulse radiolysis. For all of the DNA studied here, the formation of a pyrene dimer radical cation was accomplished quickly, within 20 micro seconds after a 8-ns electron pulse during pulse radiolysis. The results show that the minor groove of DNA offers a good space for the formation of pyrene dimer radical cations.
  • Jun Mizukami, Hiroki Sugiura, Masahiko Yamaguchi, Kumiko Mushiake
    2006 Volume 79 Issue 2 Pages 317-332
    Published: 2006
    Released: February 10, 2006
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    Optically active polyamine oligomers containing three to six (P)-5,8-bis(aminomethyl)-1,12-dimethylbenzo[c]phenanthrenes were synthesized employing the two-directional chain extension method. It was critical for the effective coupling of amines and aldehydes to precipitate imine intermediates using the appropriate solvents. UV, CD, fluorescent, and NMR spectroscopic studies revealed that the above-mentioned oligomers form multilayer structures in aqueous solvents, while they form random coil structures in methanol. Such layer structures contained helicene dyads with an anti-conformation in which the BC-rings of helicenes were stacked on each other, and 1,12-dimethyl groups were arranged in the opposite direction. A diastereomeric trimer was also synthesized, the layer structure of which was different from that of the parent trimer. The stereochemistry of the helicene moiety influenced the layer structure.
  • Atsushi Oota, Toshinobu Imai, Ayumi Yamazaki, Toru Oba, Michinori Kari ...
    2006 Volume 79 Issue 2 Pages 333-335
    Published: 2006
    Released: February 10, 2006
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    We studied the formation of 2,2′-diacyl-9,9′-bifluorenylidene from 2-acyl-9-bromofluorene via the corresponding intermediate 9-bromo-9,9′-bifluorenyl. It was found that dehydrobromination of the 9-bromo-9,9′-bifluorenyl derivatives occurred through the E2 elimination sequence, suggesting that the configuration of 9-bromo-9,9′-bifluorenyl isomers determined the stereochemistry of the product. Facile isomerization of the formed 9,9′-bifluorenylidenes may give the observed stereo-selectivity depending upon the length of the acyl side chain.
  • Kazuya Inomata, Makoto Ogawa
    2006 Volume 79 Issue 2 Pages 336-342
    Published: 2006
    Released: February 10, 2006
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    Mg/Al layered double hydroxide–oleate and –stearate intercalation compounds were successfully synthesized by the reconstruction method under hydrothermal conditions from calcined hydrotalcite. The intercalation compounds were characterized by the high structural regularity as evidenced by the sharp and intense X-ray diffraction peaks. The oleate intercalated layered double hydroxide exhibits unique physicochemical properties such as a reversible thermoresponsive change in the basal spacing and swelling in organic solvents such as n-alkanes.
  • Kazuo Nomura, Mo Liu
    2006 Volume 79 Issue 2 Pages 343-347
    Published: 2006
    Released: February 10, 2006
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    Acid phosphatase from potato was immobilized onto the surface of the external solution side of a perfluorocarboxylate ionomer membrane using a cross-linking reagent. Based on the distinct difference in membrane permeabilities to 4-nitrophenol and 4-nitrophenyl phosphate, a membrane reactor system using the immobilized enzyme has been designed for the recovery of the reaction product of enzymatic hydrolysis. To observe the recovery rate for the hydrolysis product, the flux from the external solution side to the internal solution side crossing the membrane was measured in the substrate concentration range below 1 × 10−2 mol dm−3. The recovery rate was found to obey a Michaelis–Menten type equation. The Michaelis constant for the immobilized enzyme was smaller than that for the free enzyme obtained from the kinetic properties in the bulk solution. The optimum pH value for the immobilized enzyme membrane was investigated.
  • Atsushi Miyagawa, Maria Carmelita Z. Kasuya, Kenichi Hatanaka
    2006 Volume 79 Issue 2 Pages 348-356
    Published: 2006
    Released: February 10, 2006
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    Membranes with immobilized glycoconjugate polymers were prepared and lectin adsorption was evaluated. Glycoconjugate polymers having the carbohydrates, lactose, and mannose, the amino groups of the reaction point, and a fluorescence label were synthesized, while cellulose membranes were carboxymethylated. The content of the carboxyl group was evaluated by titration. Subsequently, the glycoconjugate polymers were immobilized on the cellulose membranes by amide linkages formed by condensation reaction. Analysis of the luminescence of the fluorescence labels revealed that the glycoconjugate polymers had been immobilized on the cellulose membranes. Examination of lectin adsorption by the glycoconjugate polymer on the membrane revealed that the membrane with the immobilized mannose-having polymer adsorbed 53% of the applied ConA and the membrane with the immobilized lactose-having polymer adsorbed 83% of the applied RCA120. The membrane with immobilized glycoconjugate polymers selectively adsorbed each lectin. In addition, membranes with different types of immobilized glycoconjugate polymers were used in stacks, and in this case, the membranes selectively adsorbed lectin. Thus, membranes with immobilized glycoconjugate polymers efficiently and easily purify lectin.
  • Ayumi Ishibashi, Naotoshi Nakashima
    2006 Volume 79 Issue 2 Pages 357-359
    Published: 2006
    Released: February 10, 2006
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    We report a strong chemical structure dependence for the individual dissolution of single-walled carbon nanotubes (SWNTs) in aqueous micelles of six steroid biosurfactants including sodium cholate (SC), sodium deoxycholate (SDC), sodium taurodeoxycholate (STDC), sodium glycocholate (SGC), 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonic acid (CHAPS), and sucrose monocholate (SMC) and two sugar surfactants, n-octyl β-D-glucoside (OG) and n-decyl β-D-maltoside (DM).
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