All issues
Volume 34, Issue 11
Displaying 1-50 of 71 articles from this issue
-
JUZIRO NISHIJO, IKUKO YONETANI, KIYOSHI TAGAHARA, YUKIO SUZUTA, EMIKO ...1986 Volume 34 Issue 11 Pages 4451-4456
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermodynamic parameters for self-association of theophylline in aqueous solution adjusted to ionic strength 0.20 were determined by proton unclear magnetic resonance spectroscopy. The results obtained at pD 5.8 were as follows : ΔG°=-0.95kcal/mol at 30°C (K=4.8M-1), ΔH°=-6.3kcal/mol, and ΔS°=-18e.u. It was found that the driving force for self-association involves electrostatic, polarization, and dispersion interactions, and the contribution of hydrophobic bonding is small. A possible mode of self-association of theophylline is postulated. It was found that self-association of theophylline occurs more easily in the neutral state than in the ionized state.View full abstractDownload PDF (611K) -
MINORU TSUDA, SETSUKO OIKAWA, YORIKO OKAMURA, KATSUHIKO KIMURA, TADASH ...1986 Volume 34 Issue 11 Pages 4457-4466
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe ring substituent dependence in the NIH-shift (the migration of a hydrogen atom during aryl hydroxylation catalyzed by cytochrome P-450) was investigated by semi-empirical molecular orbital calculations. The lowest energy path, the intrinsic reaction coordinate, was found on the 3N-6 dimensional potential energy hypersurface of the protonated arene oxide ring opening (aniline and acetanilide were selected as substrates of class I, and benzene and anisole as substrates of class II). The conclusions are as follows : a) The NIH-shift occurs by a simple and common mechanism regardless of class I or class II categorization; i.e., the Meisenheimer-type intermediate having a para-quinoid structure spontaneously produced from the protonated arene oxide passes over the saddle point of hydrogen migration to an adjacent position of the aromatic ring. b) The theoretically obtained reaction rate constants reproduce quantitatively the experimental data on the retention of deuterium, on the assumption that the deuterium retention is determined by the rate constant reflecting the potential energy barrier height from the Meisenheimer-type tetrahedral intermediate to the final product. This result may suggest that the P-450-catalyzed 4-hydroxylation of aromatics involves a tetrahedral intermediate as the first product with the absence of epoxide formation.View full abstractDownload PDF (985K) -
SATORU YAMAGUCHI, HIROYUKI SHINODA, MASAMI INOUE, SABURO ENOMOTO1986 Volume 34 Issue 11 Pages 4467-4473
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidation of naphthalenes and methylbenzenes to quinones with aqueous 60% hydrogen peroxide in the presence of a 0.24% Pd(II)-sulfonated polystyrene-type resin catalyst was studied. The presence of electron-donating substituents on carbon-2 of naphthalenes accelerated the oxidation. A reaction path by way of hydroxylated intermediates to the quinones is proposed.By using the MINDO/3 method, quantum chemical indices such as the superdelocalizability for electrophilic species (SEr) and for radical species (SRr), and the net charge (Qr) of naphthalenes, methylbenzenes, and naphthols were calculated. The activity in the above reaction could be explained in terms of bothe Qr and SEr. The decrease of the selectivity was correlated with side reactions by radical species attacking the sites of largest SRr.View full abstractDownload PDF (693K) -
SABURO SHIMABAYASHI, HIDEJI TANAKA, MASAYUKI NAKAGAKI1986 Volume 34 Issue 11 Pages 4474-4478
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConcentrations of phosphate ion ([Pi]f) and calcium ion ([Ca2+]f) free from the surface of hydroxypatite (Ca10(PO4)6(OH)2; HAP) at the adsorption equilibrium of sodium dodecyl sulfate (SDS) were determined as a function of equilibrium concentration of dodecyl sulfate ion ([DS-]f). When [DS-]f was lower than its critical micelle concentration (cmc), [Pi]f increased with increase in [DS-]f owing mainly to the ion-exchange between dodecyl sulfate ion (DS-) and surface phosphate ion. However, [Ca2+]f decreased with increase in [Pi]f to maintain the solubility product of HAP constant. On the other hand, when [DS-]f was higher than the cmc, [Ca2+]f increased with increase in [DS-]f due to the binding of Ca2+ to DS- micelles. Anionic species were concomitantly liberated from the surface of HAP to maintain the electroneutrality of the surface phase. Therefore, [Pi]f increased and the amount of adsorption of DS- decreased with increase in [DS-]f.View full abstractDownload PDF (583K) -
MASAYUKI NAKAGAKI, HIROAKI KOMATSU, TETSUROU HANDA1986 Volume 34 Issue 11 Pages 4479-4485
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe estimation of the critical micelle concentration (cmc) of various lysolecithins with 2-p-toluidinylnaphthalene-6-sulfonate (TNS) and 1-anilinonaphthalene-8-sulfonate (ANS) as fluorescent probes was investigated. The fluorescence yield of TNS in palmitoyl lysolecithin micellar phase was found to be somewhat larger than that of ANS. Further, the fluorescence yield of TNS in the aqueous phase is known to be much smaller than that of ANS. Thus, TNS should be useful for estimating very small cmc values of surfactants such as lysolecithins. The cmc values of lysolecithins estimated by using TNS were 0.5mM for lauroyl lysolecithin, 63μM for myristoyl lysolecithin, 8.3μM for palmitoyl lysolecithin and 6.6μM for oleoyl lysolecithin, in 20mM Tris-HCl buffer solution (pH7.0) at 25°C. It was also found that stearoyl lysolecithin does not form micelles at room temperature, and the Krafft point is about 60°C.View full abstractDownload PDF (696K) -
MASAYUKI NAKAGAKI, HIROAKI KOMATSU, TETSUROU HANDA1986 Volume 34 Issue 11 Pages 4486-4493
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe microenvironments provided by lysolecithin micelles, surfactant (heptaethylene glycol dodecyl ether, cetyltrimethylammonium chloride, sodium dodecyl sulfate and dodecyl sulfobetaine) micelles and lecithin liposomal membranes in aqueous solutions were investigated by using dialkylthiacarbocyanine dyes as spectroscopic (absorption and fluorescence) probes. These probes give information concerning effective polarity and effective viscosity in the vicinity (microenvironment) of the probe in liposomal membranes and micelles. The microenvironment of the cyanine dyes in lysolecithin micelles have higher polarity (corresponding to that of ethanol) and lower viscosity (3-10cP) than those of other surfactant micelles and lecithin liposomal membranes. The microenvironment provided by lecithin liposomal membranes has medium polarity (1-propanol) and the highest viscosity (10-65cP) among the three kinds of amphiphilic molecular aggregates. Surfactant micelles provide microenvironments with a wide range of polarity (corresponding to ethanol, 1-propanol or 1-butanol) and lower viscosity (2-8cP) than lecithin liposomal membranes. Thus, these molecular aggregates provide microenvironments of various polarities and viscosities, and a microenvironment suitable for solubilizing and stabilizing particular drugs can be provided by choosing appropriate molecular aggregates.View full abstractDownload PDF (768K) -
SHINICHIRO TAKAHASHI, NOBUYA NAGASHIMA, YOSHIFUMI NISHIMURA, MASAMICHI ...1986 Volume 34 Issue 11 Pages 4494-4499
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction of aclacinomycin-A (ACM) with a deoxyribo-hexanucleotide pentaphosphate d(CCTAGG)2 in aqueous solution was studied by 1H, 31P nuclear magnetic resonance techniques and by visible absorption spectroscopy. From the visible absorption spectra, ACM was found to be bound by polynucleotides with binding constants of the order of 106, in the order poly(dA-dT)>poly(dC)+poly(dG)>poly(dA-dG)+poly(dT-dC). With gradual addition of ACM to d(CCTAGG), two 31P resonances newly appeared in the lower fied region as compared with d(CCTAGG) in the non-complex state, while the 31P resonance assignable to the TpA portion in the non-complexed state decreased in intensity. From these results, the chromophore of ACM is expected to be intercalated in the TpA portion of the oligo-deoxyribonucleic acid duplex. The line widths of the exchangeable proton resonances of complex in H2O were examined as a funciton of the temperature. The results suggested that ACM stabilizes the helix of d(CCTAGG)2 at a region around the intercalation site.View full abstractDownload PDF (636K) -
KO SUGAMA, KOJI HAYASHI, HIROSHI MITSUHASHI, KO KANEKO1986 Volume 34 Issue 11 Pages 4500-4507
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new glycosides named cynapanosides A (1), B (2), and C (3) which contain a new aglycone, glaucogenin D (10), were isolated from Cynanchum paniculatum, in addition to the known compounds, cynatratoside B (5) and 3β, 14-dihydroxy-14β-pregn-5-en-20-one (13). Their structures were elucidated by spectroscopic and chemical methods. The results led us to propose a structure revision of glaucogenin B (11).View full abstractDownload PDF (854K) -
HIROSHI SAI, SUGURU TAKATSUTO, NOBUO IKEKAWA, YOKO TANAKA, HECTOR F. D ...1986 Volume 34 Issue 11 Pages 4508-4515
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to determine the structure of a new metabolite of 25-hydroxy-24-epivitamin D2, 1, 25-dihydroxy-22-dehydro-24-homo- and 26-homo-vitamin D3 were synthesized. The saturated analogues at the C-22 position of these homovitamin D3 compounds were also synthesized. For the construction of the side chain of these homo-analogues, the orthoester Claisen rearrangement of the allylic alcohol was employed.Assay of binding of these compounds with the chick intestinal cytosol receptor protein for 1, 25-(OH)2D3 was carried out by the displacement method. The results indicated that these homovitamin D3 analogues are as active as 1, 25-(OH)2D3. The bone calcium-mobilizing activities of these compounds were equivalent to that of 1, 25-(OH)2D3.View full abstractDownload PDF (859K) -
MASAHIKO SEKI, HITOSHI KUBOTA, TAMON MORIYA, MASAFUMI YAMAGISHI, SHIGE ...1986 Volume 34 Issue 11 Pages 4516-4522
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSC-Acylation of α-isocyanosuccinate having an aspartic acid skeleton, Dakin-West and Friedel-Crafts reactions with 2-oxazolin-5-oneacetate (aspartic acid azlactone) were found to be efficient methods for the preparation of various β-amino-γ-ketobutyric acid derivatives.View full abstractDownload PDF (721K) -
HIROKI TAKAHATA, KYOKO YAMABE, TOSHIAKI SUZUKI, TAKAO YAMAZAKI1986 Volume 34 Issue 11 Pages 4523-4526
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA common intermediate, the quinolizidine (5) obtained by annulation of a cyclic thioimidate (3) with Nazarov's reagent (4) in the presence of mercuric chloride, was stereospecifically transformed into (±)-epiupinine (1) and (±)-lupinine (2).View full abstractDownload PDF (491K) -
HIROSHI KASHIHARA, HIROSHI SHINOKI, HIROSHI SUEMUNE, KIYOSHI SAKAI1986 Volume 34 Issue 11 Pages 4527-4532
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDuring the course of synthetic studies on the 5, 6-disubsituted 4-oxo-tetrahydro-2-pyroneskeleton in connection with biologically active compounds, we have found a convenient procedure for the regioselective introduction of a double bond in methyl alkyl ketones and a novel synthetic method for indan derivatives.View full abstractDownload PDF (626K) -
TSUTOMU HATANO, SHIN HATTORI, TAKUO OKUDA1986 Volume 34 Issue 11 Pages 4533-4539
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new dimeric hydrolyzable tannins, named coriariins C (3), D (4) and E (5), and a new monomeric tannin, coriariin F (6), have been isolated from the leaves of Coriaria japonica A. GRAY along with rugosin B (7), gemin D (8) and strictinin, and the structures of new tannins have been established upon the basis of chemical and spectroscopic evidence.View full abstractDownload PDF (744K) -
YASUO FUJIMOTO, MITSURU SATOH1986 Volume 34 Issue 11 Pages 4540-4544
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(±)-2, 4, 5- and 2, 4, 8-Trihydroxy-1-tetralones (2, 9, 3, 11) were synthesized from juglone, and their cytotoxic activities against Yoshida sarcoma cells were examined. The trihydroxytetralones were more cytotoxic than dihydroxytetralones. While the configuration of the hydroxyl groups in the alicyclic ring scarcely affected the cytotoxicity against Yoshida sarcoma cells, the position of the hydroxyl groups in the aromatic ring seem to be important. The 2, 4, 8-trihydroxytetralones (3, 11) were more cytotoxic than the 2, 4, 5-trihydroxy derivatives (2, 9).View full abstractDownload PDF (534K) -
TAKUSHI KURIHARA, MITSUKO HANAKAWA, SHINYA HARUSAWA, RYUJI YONEDA1986 Volume 34 Issue 11 Pages 4545-4553
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of 3-acylindoles [3-indolecarbaldehyde (1), 3-acetylindole (12), 3-benzoylindole (13), and N-substituted 3-indolecarbaldehydes (20a-d)] with diethyl phosphorocyanidate (DEPC) in the presence of lithium cyanide (LiCN) are described. Treatment of 1 with DEPC and LiCN gave a mixture of (E)- and (Z)-3-cyanomethylene-1-diethylphosphono-2-hydroxyindolines (2 and 3). On the other hand, reaction of 12, 13 and 20a-d with DEPC and LiCN afforded 2-cyano-3-indoleacetonitrile derivatives (16, 19 and 21a-d). Strong base-induced cycloaddition reactions of 2-cyano-1-methyl-3-indoleacetonitrile (21a) with carbon-carbon triple bonds were carried out and gave the corresponding condensation products, 1-amino-4-cyanocarbazoles (22a-e), 6-amino-11-cyanobenzo[b]carbazole (23), pyrido[4, 3-b]carbazole (25), and pyrido[3, 4-b]carbazole (26), in moderate yields.View full abstractDownload PDF (933K) -
KOUICHI YOKOI, KATSUHIKO NAGAOKA, TOSHIAKI NAKASHIMA1986 Volume 34 Issue 11 Pages 4554-4561
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of azinomycins A and B, new antitumor antibiotics produced by a strain of Streptomyces, were determined on the basis of their spectral and chemical properties. The structures of three related metabolites coproduced with these antibiotics were also determined.View full abstractDownload PDF (766K) -
TSUTOMU MIMURA, MASARU OKABE, MIKIO SATAKE, TSUTOMU NAKANISHI, AKIRA I ...1986 Volume 34 Issue 11 Pages 4562-4568
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe fatty acid and sterol compositions of the marine tunicate Salpa thompsoni from the Antarctic Ocean are reported. Of the 21 fatty acids identified, the acids 16 : 0, 20 : 5ω3, and 22 : 6ω3 were present at high concentrations. The salpa also contained various C26, C27, C28, and C29 sterols with three Δ5-sterols, i.e., cholesterol (6), (22E)-(24ξ)-24-methylcholesta-5, 22-dien-3β-ol (9), and 24-methylene-cholest-5-en-3β-ol (11) as the main constituents. The presence of eight related pairs of Δ5-sterols and 5α-stanols with identical side chains was characteristic. Desmosterol (8) and sitostanol (or C-24 epimer) (17) were found for the first time in salpas. Furthermore, the hemolytic active components of methanol extract of the salpa were examined. The total fatty acids fraction was strongly hemolytic, and detailed examination of each component acid showed the polyunsaturated acids 22 : 6ω3 and 20 : 5ω3 to be most potent.View full abstractDownload PDF (711K) -
TAKEO HIGASHINO, SUSUMU SATO, AKIRA MIYASHITA, TATSUHIKO KATORI1986 Volume 34 Issue 11 Pages 4569-4576
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Reissert reaction of 1-phenyl-1H-pyrazolo[3, 4-d]pyrimidine (4) in anhydrous methylene chloride using benzoyl chloride, trimethylsilyl cyanide, and a catalytic amount of aluminium chloride gave the corresponding Reissert compound (3, 5-benzyol-4, 5-dihydro-1-phenyl-1H-pyrazolo[3, 4-d]pyrimidine-4-carbonitrile) in 95% yield.The alkaline hydrolysis of 3 in methanol resulted in the formation of 4, benzoic acid (7), and the 4, 4'-dimer (9) of 4. The acid hydrolysis in dimethyl sulfoxide and in methanol proceeded with ring fission to give 5-amino-α-benzamido-1-phenyl-1H-pyrazole-4-acetonitrile (13), the acetamide (14), and the acetate (15). Compound 3 reacted with sodium hydride in dimethylformamide to give 4, 9, 1-phenyl-1H-pyrazolo[3, 4-d]-pyrimidine-4-carbonitrile (20), α, 1-diphenyl-1H-pyrazolo[3, 4-d]pyrimidin-4-ylmethyl benzoate (21), and O-benzoylmandelonitrile (22).In the present paper, we compare the chemical properties of 3 with those of the isoquinoline Reissert compound (1, 2-benzoyl-1, 2-dihydro-1-isoquinolinecarbonitrile).View full abstractDownload PDF (686K) -
MASAYUKI SATO, NAOKI YONEDA, CHIKARA KANEKO1986 Volume 34 Issue 11 Pages 4577-4584
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel method for the introduction of an alkyl group at the 5-position of 1, 3-dioxin-4-ones is described. Reaction of 5, 6-unsubstituted 1, 3-dioxin-4-ones with N-halosuccinimide in acetic acid followed by treatment with a base gave 5-bromo- and 5-iodo-1, 3-dioxin-4-ones, which were converted to the corresponding 5-alkylated dioxinones either by palladium-catalyzed cross-coupling or by photochemical allylation reactions. Successful conversion of 5-ethyl-2, 2-dimethyl-1, 3-dioxin-4-one either to a 5-ethyl-1, 3-oxazin-4-one derivative or an α-ethylformylacetate upon heating in xylene demonstrated that these 5-substituted 1, 3-dioxin-4-ones can serve as chemical equivalents for substituted formylketenes.View full abstractDownload PDF (857K) -
HIDEO INOUE, NAOMI SAITO, TOHRU UEDA1986 Volume 34 Issue 11 Pages 4585-4589
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of N3, 5'-O-dibenzoyl-2', 3'-O-isopropylidene-5-bromouridine (1) with dimethyl malonate in the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene afforded a 5-malonate ester derivative (2) in high yield. Uridine-5-acetic acid (7) and its methyl ester (4), minor nucleosides in transfer ribonucleic acids, could be readily obtained from 2 via removals of one carboxyl function and protecting groups. Treatment of N3, 5'-O-dibenzoyl-2', 3'-O-isopropylideneuridine (8) with the carbanion of ethyl acetoacetate caused degradation of the base moiety to give an N3-benzoyl-ribosylurea derivative (9) in good yield. Possible mechanisms of these reactions are proposed.View full abstractDownload PDF (657K) -
ISAO KITAGAWA, MOTOMASA KOBAYASHI, CUI ZHENG, YUTAKA KIYOTA, MAYUMI OH ...1986 Volume 34 Issue 11 Pages 4590-4596
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new polyhydroxysterols, named xeniasterol-a (4), xeniasterol-b (5), xeniasterol-c (6), and xeniasterol-d (7), were isolated from an Okinawan soft coral of Xenia sp. (Xeniidae). On the basis of chemical and physicochemical evidence, the structures of xeniasterol-a, -b, -c, and -d have been elucidated respectively as 7-O-acetylergost-22E-ene-3β, 5α, 6β, 7β-tetraol (4), 7-O-acetylergosta-3β, 5α, 6β, 7β-tetraol (5), gorgosta-3β, 5α, 6β-triol (6), and 7-O-acetylgorgosta-3β, 5α, 6β, 7β-tetraol (7). Germacrene-c (1) was also isolated from the same soft coral together with two guaiane-type compounds (2, 3), and it has been shown that germacrene-c (1) is readily air-oxidized to yield these cyclization products (2, 3).View full abstractDownload PDF (769K) -
HIROSHI TAKAHASHI, YUMIKO KUBOTA, FANG LIN, SHAOSHUN LI, MASAYUKI ONDA1986 Volume 34 Issue 11 Pages 4597-4604
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of substitutents on the formation of products in the reactions of 2"-methoxymethoxychalcone epoxides under acidic conditions has been examined. Regardless of the 6"-substitutent, the presence of a 4'-hydroxyl group results in the exclusive formation of flavanonols. The presence of a 4'-methoxyl group directs the reactions toward the competitive formation of flavanonols and glycol monomethyl ethers or toward the exclusive formation of glycol monomethyl ethers, depending on the bulk of the 6"-substituent.View full abstractDownload PDF (891K) -
TERUYO MATSUMOTO, MASAKO OHSAKI, MICHIYO SUZUKI, YOSHIKAZU KIMURA, SHI ...1986 Volume 34 Issue 11 Pages 4605-4612
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy employing various novel reactions developed in our synthetic studies on 4-demethoxy-adriamycin and 4-demethoxydaunorubicin, three examples of the title compounds (7a-c) were prepared from (R)-2, 5, 12-trihydroxy-1, 2, 3, 4-tetrahydro-6, 11-naphthacenedione-2-carboxylic acid (9). While 7a-c showed marked cytotoxicity against P388 in vitro, it was found that 7a (carrying a nonanoyl group at the C9-position) was ineffective against P388 in vivo.View full abstractDownload PDF (925K) -
TERUYO MATSUMOTO, MASAKO OHSAKI, MICHIYO SUZUKI, YOSHIKAZU KIMURA, SHI ...1986 Volume 34 Issue 11 Pages 4613-4619
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title compounds, (+)-13-methyl-13-dihydro-4-demethoxydaunorubicin hydrochloride (8·HCl) and (+)-13-methyl-13-dihydrodaunorubicin hydrochloride (9·HCl), were prepared from (+)-4-demethoxydaunomycinone (13) and (+)-daunomycinone (18), respectively, by silylation of the C7-hydroxy group, addition of methylmagnesium bromide to the C13-carbonyl group, and direct glycosidation of the 7-O-silyl anthracyclinones with the daunosamine derivative (anthracycline numbering). In the P388 in vitro test, 8·HCl was several hundred-fold more active than adriamycin hydrochloride (1·HCl). Notable anticancer activity, equivalent to that of adriamycin hydrochloride, was also observed in the P388 in vivo test of 8·HCl.View full abstractDownload PDF (921K) -
TAKUSHI KURIHARA, MASUO MIKI, KAZUNORI SANTO, SHINYA HARUSAWA, RYUJI Y ...1986 Volume 34 Issue 11 Pages 4620-4628
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBoron trifluoride-catalyzed allylic rearrangement of α, β-unsaturated ketone cyanophosphates (2, 6 and 12) gave (Z)-4-diethylphosphonooxy-2-butenenitriles (3, 8 and 13), while α, β-unsaturated aldehyde cyanophosphates (17a-c) afforded (E)-4-diethylphosphonooxy-2-butenenitriles (18a-c) stereoselectively. The stereo- and regioselective reaction of 2 with several kinds of aromatics in the presence of boron trifluoride etherate afforded (Z)-4-aryl-2-methyl-2-butenenitriles (20) via the SN2' reaction. On the other hand, treatment of 2 with 1-subsituted indoles in the presence of boron trifluoride etherate gave 1-amino-2-methylcarbazole derivatives (23a-c).View full abstractDownload PDF (1002K) -
HIROSHI SUEMUNE, HIROSHI MARUOKA, SEITARO SAEKI, KIYOSHI SAKAI1986 Volume 34 Issue 11 Pages 4629-4634
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis paper describes a conversion of (-)-limonen-10-ol to the key intermediate (1) for 11-deoxyprostaglandin. The 3, 4-cis-disubstituted cyclopentanone (2), which was easily obtained from (-)-limonen-10-ol in a stereocontrolled fashion by means of Rh(I)-catalyzed cyclization via the 4-pentenal derivative, could be directly converted to the bicyclo[3.3.0]octenone (3) by treatment with KHSO4 in boiling benzene. Compound 3 with a double bond at the favorable position was converted to 1 by way of fission of the double bond and subsequent modification of substituents on the five-membered ring.View full abstractDownload PDF (732K) -
TAIKO ODA, YOSHIHIRO SATO1986 Volume 34 Issue 11 Pages 4635-4640
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stereochemistry of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-dependent hydrogenation was investigated by the conversion of (-)-dehydrogriseofulvin (1) to (+)-griseofulvin (2a) by the use of a partially purified enzyme system of Streptomyces cinereocrocatus in the presence of (4R)- or (4S)-[4-2H1]NADPH. The results of 270MHz proton nuclear magnetic resonance spectroscopy indicated that the origin of the 6'α-hydrogen of 2a is a hydride ion donated by pro-4R-hydrogen of NADPH.View full abstractDownload PDF (668K) -
ISAO KITAGAWA, CUI ZHENG, YANG CAI, MOTOMASA KOBAYASHI, YOSHIMASA KYOG ...1986 Volume 34 Issue 11 Pages 4641-4652
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo pairs of diastereomeric diterpenes, xeniolone (1) and isoxeniolone (3), and hydratoxeniolone (16) and hydratoisoxeniolone (18), were isolated, together with their putative biogenetic precursor, germacrexeniolone (20), from an Okinawan soft coral of Xenia sp. (Xeniidae). On the basis of chemical and physiochemical evidence, the absolute stereostructures of these five diterpenes have been elucidated. It has also been shown that germacrexeniolone (20) is gradually air-oxidized to yield xeniolone (1) and isoxeniolone (3) upon standing, while in an aqueous acetone solution, it yields hydratoxeniolone (16) and hydratoisoxeniolone (18).View full abstractDownload PDF (1297K) -
TAKEHIRO AMANO, KENSEI YOSHIKAWA, TOSHIHISA OGAWA, TATSUHIKO SANO, YUT ...1986 Volume 34 Issue 11 Pages 4653-4662
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-phenylpropionic acids substituted with a C2-C6 alkenyl group at the para position was synthesized by hydrolysis of the corresponding esters prepared by a new nickel-catalyzed coupling reaction of aryl Grignard reagents and 2-bromopropionic acid ester. Among the 2-(4-alkenylphenyl)propionic acids thus obtained, 2-[4-(2-metyl-1-propenyl)phenyl]propionic acid showed the most potent antiinflammatory activity in the carrageenin edema test, while 2-[4-(3-methyl-2-butenyl)phenyl]propionic acid showed almost the same activity and significantly lower toxicity in comparison with those of ibuprofen.View full abstractDownload PDF (956K) -
KEIKO WAKITA, MASAFUMI YOSHIMOTO, SHUICHI MIYAMOTO, HIDETOSHI WATANABE1986 Volume 34 Issue 11 Pages 4663-4681
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the calculation of the aqueous solubility of organic compounds, we defined new fragment solubility constants (fs) which were empirically determined on the basis of compiled data from the literature. First, 6 fundamental fs values were determined from data on 46 liquid alliphatic hydrocarbons. THese fs values were fixed, and data on 249 liquid aliphatic compounds with diverse functional groups were employed to optimize another 19 fs values of the groups. Then, 15 fs values of aromatic compounds were calculated based on the solubility data on 58 aromatic liquids and the aliphatic fs values.It has been shown that there is a linear relationship between the logarithims of the aqueous solubilities of organic liquids and the octanol-water partition constants (log P), and that the water solubilities can be calculated by using the correlation equation and log P values. The present paper is concerned with a method to calculate the aqueous solubilities of organic liquids simply, directly and more accurately on the basis of fs values. Furthermore, the calculation of the water solubilities of organic solids was attempted with a correction based on the melting points, in addition to using the fs values.View full abstractDownload PDF (1501K) -
HIDEJI ITOKAWA, HAJIME MATSUMOTO, KENJI MIZUNO, KINZO WATANABE, HIROSH ...1986 Volume 34 Issue 11 Pages 4682-4686
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel germacranolides (torilolide and oxytorilolide) were isolated from Torilis japonica (HOUTT.) DC. and their structures were determined by X-ray diffraction analysis and from spectral data.View full abstractDownload PDF (499K) -
HITOSHI NOHTA, SHUNYA NOMA, YOSUKE OHKURA1986 Volume 34 Issue 11 Pages 4687-4693
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe previously reported assay method for catechol-O-methyltransferase, which uses 2-(3, 4-dihydroxyphenyl)naphtho[1, 2-d]thiazole as a fluorogenic substrate, was applied to the assay of the enzyme in human and rat erythrocyte membrane and soluble fractions, and various rat tissue preparations, with some modifications. The m- and p-methylated products formed enzymatically were determined by normal-phase high-performance liquid chromatography with fluorescence detection. The detection limits for the m- and p-methylated products were 1 pmol per assay tube (50fmol per injection volume of 50μl) in each case. No difference among the preparations was observed in optimal reaction conditions for the enzyme, but the ratio of m- and p-methylated products and the Michaelis constant values for the substrate and S-adenosyl-L-methionine (methyl donor) varied from preparation to preparation.View full abstractDownload PDF (717K) -
FUMIKO ISHIHARA, HIROSHI MASHIKO, HIDENOBU TAKAHASHI1986 Volume 34 Issue 11 Pages 4694-4702
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen the pseudoglobulin fraction of porcine plasma was gel-filtered through a column of Sephadex G-150, two fractions, from which kinin was released on incubation with trypsin [EC3.4.21.4], were observed. This indicates the presence of two kininogens with different molecular weights in the plasma. The larger-molecular-weight kininogen fraction had the ability to correct the abnormal clotting time of human high-molecular-weight (HMW) kininogen-deficient plasma, Fitzgerald plasma. The smaller-molecular-weight kininogen fraction did not show this ability. Thus, the fraction showing the ability to correct the abnormal clotting time of Fitzgerald plasma was considered to contain a kininogen corresponding to that purified as an HMW kininogen from bovine, human, horse and rat plasma. The other fraction may contain porcine low-molecular-weight (LMW) kininogen.The porcine HMW kininogen was isolated by a modification of the purification method for horse HMW kininogen. The ability of the isolated HMW kininogen obtained to correct the abnormal clotting time of Fitzgerald plasma was in proportion to the amount of the preparation used. When this HMW kininogen preparation was incubated with purified porcine plasma kallikrein [EC 3.4.21.8], the release of bradykinin was observed.View full abstractDownload PDF (1200K) -
SHUICHI HORIE, TAKAFUMI WATANABE, TETSUYA SUGA, YOSHIHIRO TOCHINO1986 Volume 34 Issue 11 Pages 4703-4707
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnzyme activities of hepatic peroxisomes were examined in spontaneously diabetic non-obese diabetic (NOD) mice. Peroxisomal fatty acid β-oxidation activity in the NOD diabetic mouse was the same as that of the ICR mouse. Sodium glutamate-induced obesity did not affect peroxisomal enzymes. The results indicate that peroxisomal β-oxidation does not increase in the insulin-deficient mouse. Furthermore, considering that the onset of diabetes in the NOD mouse is around 13 weeks after birth, these findings suggest that hepatic peroxisomal β-oxidation is utilized mainly in the acute state, not in the chronic state, in order to obtain adenosine triphophate urgently for cellular demands.View full abstractDownload PDF (612K) -
TAKASHI ABIKO, HIROSHI SEKINO1986 Volume 34 Issue 11 Pages 4708-4717
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDeacetyl-thymosin β10 was synthesized by a conventional solution method, by assembling seven peptide fragments followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The synthetic deacetyl-thymosin β10 increased the entire peripheral T-cell population and a helper T-cell subset when incubated in vitro with blood obtained from a uremic patient with tuberculosis, but a suppressor/cytotoxic T-cell subset was unaffected under these conditions.View full abstractDownload PDF (1143K) -
TAKAKO YOKOZAWA, NAOMI SUZUKI, HIKOKICHI OURA, GEN-ICHIRO NONAKA, ITSU ...1986 Volume 34 Issue 11 Pages 4718-4723
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn attempt made to clarify the nature of the active components contained in rhubarb which show the improving effects on uremic symptoms. The progress of fractionation and purification was monitored by measuring the levels of blood urea nitrogen, creatinine, methylguanidine, and guanidinosuccinic acid after administration of each fraction to rats. Fraction II was found to have a blood urea nitrogen-decreasing effect among fractions I to V obtained by Sephadex LH-20 column chromatography. Fraction II-3, obtained by further fractionation of fraction II, was found to have a uremia-alleviating effect, causing significant decreases in blood urea nitrogen, creatinine, methylguanidine, and guanidinosuccinic acid levels. Purification of fraction II-3 by partition between ethyl acetate and H2O resulted in recovery of the blood urea nitrogen-decreasing activity in the aqueous phase, which was found to contain mainly proanthocyanidin oligomers.View full abstractDownload PDF (585K) -
SHIGENORI IWAI, AKIHIRO IMURA, YASUHIKO INOUE, HIDEO INOUE, KAZUNOBU M ...1986 Volume 34 Issue 11 Pages 4724-4730
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGene I and II for human nerve growth factor β-subunit (hNGF) (118 amino acids) were synthesized by enzymatic joining of 45 oligodeoxynucleotides with chain lengths of ca. 17, which were obtained by the phosphotriester solid-phase synthesis. Gene I contained the methionine codon downstream of a restriction site, Cla I, for direct expression under the control of E. coli trp promoter, inserted in a plasmid pGH-L9 (M. Ikehara et al., Proc. Natl. Acad. Sci., 81, 5956 (1984)). Gene II coded for a fused protein containing two-thirds of human growth hormone as well as the sequence Ile-Glu-Gly-Arg, in front of the amino acid sequence of hNGF. Both genes were amplified in E. coli by ligation to restriction sites for Cla I and Sal I of pGH-L9 followed by transformation of E. coli. The molecular weight of the expressed products was estimated by electrophoresis on acrylamide gel. The structure of the gene was characterized by restriction analysis and sequencing.View full abstractDownload PDF (1023K) -
HIROSHI HARA, ICHITOMO MIWA, JUN OKUDA1986 Volume 34 Issue 11 Pages 4731-4737
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a recent paper, we reported that glucokinase in pancreatic islets might be a critical site which mediates the inhibition of glucose-stimulated insulin secretion by alloxan and ninhydrin. The action mechanisms of the two agents on rat liver glucokinase (instead of islet glucokinase) were studied here.Both alloxan and ninhydrin irreversibly inhibited rat liver glucokinase in concentration-dependent manners. The inhibitory effects of alloxan and ninhydrin on glucokinase were blocked by the presence of hexoses (D-glucose and D-mannose) that serve as substrates of the enzyme. The blockade provided by D-glucose showed α-anomeric preference, as was also observed in the phosphorylation of D-glucose by glucokinase. Protection against the inhibition of glucokinase by alloxan or ninhydrin was also afforded by D-mannoheptulose, a competitive inhibitor of the enzyme with respect to D-glucose. These results suggest that the inhibitory sites of alloxan and ninhydrin are at or near the substrate-binding site of glucokinase.View full abstractDownload PDF (736K) -
TERUTAKA TAKAHASHI, MASAAKI MORI, YUKO UEZONO, HIROKAZU MAKITA, YUTAKA ...1986 Volume 34 Issue 11 Pages 4738-4743
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe limiting size of enteric-coated preparations for which it is possible to evaluate the bioavailability by using gastric-acidity-controlled rabbits (GAC-rabbits) was investigated. Entericcoated preparations with different diameters were administered to GAC-rabbits, and drug bioavailability from each preparation was evaluated. In the case of enteric-coated granules, there was no problem in evaluating the bioavailability. However, in the case of enteric-coated tablets, the maximum size for which it was possible to evaluate the bioavailability was 4.1mm in diameter. The results indicate that the use of GAC-rabbits in bioavailability studies of enteric-coated preparations is restricted by the size of the preparations.View full abstractDownload PDF (730K) -
LUCY SAI CHEONG WAN, THANGARAJAH JEYABALAN1986 Volume 34 Issue 11 Pages 4744-4752
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of binding liquids-water, alcohol and mixtures of the two on the pelletisation of three materials of differing solubility in water or alcohol-lactose, paracetamol and phenacetin was studied. It was found that the high solubility of lactose in water is not the only parameter affecting pellet growth properties but it is also the greater wetting of lactose particles due to surface tension lowering by alcohol in water-alcohol mixtures. Paracetamol pellets prepared with water were small and weak but those prepared with alcohol or water-alcohol mixtures were larger and of a greater strength due to the greater solubility of paracetamol in alcohol relative to that in water. Phenacetin when pelletised with water, alcohol or water-alcohol mixtures were very soft and fragile. This suggests that for very hydrophobic material such as phenacetin, it is not sufficient to be highly soluble in alcohol but solubility in water is essential.View full abstractDownload PDF (886K) -
KENJI MATSUYAMA, HIDEYUKI SAWAHARA, ATSUKO NODA, SHIGERU GOTO, SADAO I ...1986 Volume 34 Issue 11 Pages 4753-4759
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of environmental temperature on cytochrome P-450 and the associated electron transfer system was studied in male rats. Rats kept at 15°C for two weeks (group A) showed a significant increase in the activity of nicotinamide adenine dinucleotide phosphate reduced form (NADPH)-cytochrome c (P-450) reductase, whereas they showed a slight reduction in the content of cytochrome P-450 when compared with rats kept at 30°C for two weeks (group B). Further, aniline hydroxylase activity in group A increased significantly, while aminopyrine N-demethylase activity was unchanged. The activity of NADH-cytochrome b5 reductase and the content of cytochrome b5 showed no significant difference between the two groups. From the endocrinological viewpoint. the serum level of 3, 5, 3'-triiodothyronine (T3) in group A was higher than that in group B. The differences in enzyme activity and content were observed from 4d after the start of exposure of rats to each temperature.View full abstractDownload PDF (738K) -
YOSHINOBU NAKAI, KEIJI YAMAMOTO, KATSUHIDE TERADA, TOSHIO OGUCHI, SATO ...1986 Volume 34 Issue 11 Pages 4760-4766
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe physicochemical properties of drug molecules in a mixture with montmorillonite or pillar interlayer montmorillonite (PILM) were studied by using differential scanning calorimetry (DSC), powder X-ray diffraction and infrared (IR) spectroscopy. The DSC and IR data indicated that benzoic acid was converted to ionic species by heating to 400K in PILM200 and PILM400 mixtures, whereas benzoic acid molecules partially existed in an amorphous state in both montmorillonite and PILM600 mixtures.The decomposition rate of aspirin in the montmorillonite mixtures was studied at 40°C and 0, 31.3 and 79% relative humidities (RH). Asprin was decomposed rapidly at 0% RH as compared with 79% RH in the PILM mixtures. This result indicates that the aspirin did not react with the bulk water but with active water adsorbed on the internal pore surfaces of PILM.View full abstractDownload PDF (701K) -
SHUU MATSUMOTO, HIDEYO IMANISHI1986 Volume 34 Issue 11 Pages 4767-4774
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of recombinant human interferon (IFN)-gamma (Met-Gln form), which has the same amino acid sequence as natural human IFN-gamma except for the N-terminal methionine, on various cell-mediated cytotoxicities were studied in vitro comparatively with those of natural human IFN-alpha and -beta. The augmentations of natural killer (NK) and antibody-dependent cell-mediated cytotoxic (ADCC) activities against tumor cells by IFN-gamma (Met-Gln form) were equivalent or somewhat inferior to those by the natural IFNs. However, the augmentation of ADCC activity against chicken red blood cells (CRBCs) by IFN-gamma (Met-Gln form) was superior to those by natural IFNs. This prominent effect of IFN-gamma (Met-Gln form) was considered to be mediated by monocytes contained in the mononuclear cell preparation used as effector cells. As expected, IFN-gamma (Met-Gln form) actually augmented antibody-dependent monocyte-mediated cytotoxicity against CRBCs more effectively than the natural IFNs. IFN-gamma (Met-Gln form) also enhanced macrophage-mediated tumor cytotoxicity, like other preparation of recombinant IFN-gamma. The NK-augmentation by IFN-gamma (Me-Gln form) was further increased by combination with indomethacin, and the effect was completely reversed by further addition of prostaglandin E2 (PGE2). However, these agents had no effect on the NK-augmentation by natural IFN-beta. These results suggest that IFN-gamma (Met-Gln form) activates macrophages (rather than NK and killer (K) cells) to kill tumor cells and release PGs more effectively than IFN-alpha and -beta.View full abstractDownload PDF (836K) -
SHUU MATSUMOTO, HIDEYO IMANISHI1986 Volume 34 Issue 11 Pages 4775-4781
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe examined the effects of recombinant human interferon (IFN)-gamma, having Met-Gln at the N-terminal, on the in vitro production of phagosomal and extracellular activated oxygen species by human monocytes after phagocytosis and compared the results with those for natural human IFN-alpha and -beta. The phagosomal production was measured by a new method using luminol-binding microspheres and the extracellular production was measured by two conventional methods using luminol sulution and opsonized zymosan or yeast particles. We also examined the effect of the IFN-gamma on the phagocytic activity of human monocytes by using luminol-binding microspheres. It was found that IFN-gamma remarkably augmented both phagosomal and extracellular production of activated oxygen species after phagocytosis in a dose-dependent fashion. However, IFN-alpha and -beta had a weak effect on the phagosomal production only at the highest dose tested. The natural IFNs also augmented moderately or slightly the extracellular production stimulated by opsonized zymosan but not opsonized yeast particles. IFN-gamma augmented the phagocytic activity of human monocytes. THese results demonstrated that the human monocytes treated with the IFN-gamma actually produced a larger quantity of phagosomal activated oxygen species than those treated with the natural IFNs, and the extracellular production did not always reflect the phagosomal production.View full abstractDownload PDF (814K) -
TAKABUMI NAGAI, TAKUICHI MIKI, ITSUMARO KUMADAKI1986 Volume 34 Issue 11 Pages 4782-4786
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the presence of aluminum chloride, 1, 1, 1-trifluoro-2-hexanone reacts as an enophile with several allyl compounds to give trifluoromethylated homoallyl alcohols. α, α, α-Trifluoroacetophenone reacts similarly with aliphatic allyl compounds, but its reaction with allylbenzene is too slow to be useful for the synthesis of fluorine compounds.View full abstractDownload PDF (610K) -
KEISHIRO MIYAKE, NOBUYASU MIZUNO, HIROSHI TERADA1986 Volume 34 Issue 11 Pages 4787-4796
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe high-performance liquid chromatography (HPLC) of various compounds on an ODS (octadecylsilane) stationary phase was carried out with mobile phases containing vaious amounts of organic solvents, and the retention behavior was analyzed in terms of the partition coefficient between octanol and water P<oct>. It was found that the capacity factor k' increased linearly with Poct. However, this relation was dependent on the hydrogen-bonding ability of the compounds. The retention behaviors of non-hydrogen bonders, hydrogen acceptors and amphiprotic compounds were different.It was shown that from the results of HPLC on an ODS column, values of Poct of various compounds can be determined accurately and simply, by a single equation, when the hydrogen-bonding property of the compounds is take into account. The accuracy of the estimated Poct value increased with decrease in the concentration of the organic solvent in the mobile phase.View full abstractDownload PDF (843K) -
HARUKO KAMEDA, YOSHIO MONMA, TSUNEYOSHI TANABE1986 Volume 34 Issue 11 Pages 4797-4804
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe β-receptor agonist potency and α-receptor-blocking action of labetalol were investigated in tracheal smooth muscles of guinea pigs. With resting-tone preparations and methacholine-contracted preparations of trachea, labetalol produced relaxation and behaved as a partial agonist. The maximum relaxing response to labetalol of methacholine-contracted preparations was markedly smaller than that of the resting-tone preparations. The results suggest that the relaxing action of labetalol is weaker on the high tracheal tone induced by the cholinergic agonist, methacholine. With resting-tone preparations, norepinephrine and phenylephrine produced relaxation, but after the β-receptors were blocked, these drugs produced contraction. These findings confirm the existence of α-excitatory receptors and the predominance of β-receptors over α-receptors in the trachea. When labetalol was administered first, it showed β-receptor agonist action and inhibition of contraction of the resting-tone preparations due to α-receptors. When labetalol was administered secondly, it did not show β-receptor agonist action but exerted α-adrenoceptor-blocking action. These results suggest that labetalol produces relaxation of the tracheal preparations in guinea pigs through its β-receptor partial agonist action and α-receptor-blocking action. However, it is thought that this relaxing effect of labetalol might be small when the β-adrenoceptor reserve in the trachea is occluded or exhausted by pretreatment with a β-receptor blocker or a cholinergic agonist, methacholine.View full abstractDownload PDF (797K) -
SUZUMITSU KUNO, KENICHI AKAJI, MITSURU AONO, ATSUSHI TAKAGI, MOTOYUKI ...1986 Volume 34 Issue 11 Pages 4805-4810
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCanine gastrin-releasing polypeptide (cGRP, characterized as a bombesin-like 27-residue peptide) was synthesized by successive azide condensations of 7 peptide fragments of established purity, followed by deprotection with trifluoromethanesulfonic acid in trifluoroacetic acid. Prior to deprotection, the Met(O) residue in the protected cGRP was reduced by brief treatment with phenylthiotrimethylsilane in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate. The homogeneous HPLC-purified product induced a significant increase of immunoreactive gastrin level in rat plasma, like synthetic human GRP.View full abstractDownload PDF (701K) -
SUZUMITSU KUNO, WEI LI, NOBUTAKA FUJII, HIDEKI ADACHI, KIYOSHI BESSYO, ...1986 Volume 34 Issue 11 Pages 4811-4816
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGln15-motilin was synthesized in a conventional manner by assembling seven peptide fragments followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The usefulness of phenylthiotrimethylsilane for the reduction of Met(O) was confirmed. This motilin analog was as biologically active as synthetic motilin in terms of contraction of rabbit duodenal muscles, but in radioimmunoassay it was only about 25% as reactive with antiserum raised against synthetic porcine motilin.View full abstractDownload PDF (664K) -
ATSUKO NOSE, TADAHIRO KUDO1986 Volume 34 Issue 11 Pages 4817-4820
Published: November 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe selective reduction of imines with the diborane-methanol system was investigated. This system reduced imines quantitatively, and other functional groups tested were unaffected.View full abstractDownload PDF (447K)