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HIDEAKI UMEYAMA, TSUNEJI NAGAI, HISASHI NOGAMI
1971 Volume 19 Issue 3 Pages
441-447
Published: March 25, 1971
Released on J-STAGE: March 31, 2008
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Solubility properties of L-tryptophan in aqueous solution was discussed on the basis of the effects of 3rd component on the optical rotatory dispersion (ORD) and on the adsorption by carbon black. ORD data showed the optical rotation of L-tryptophan around 450 mμ was suitable in analyzing the effect of 3rd component on it. Adsorption data indicated the respective hydrophobicities of the present 3rd components. Alcohols and glycols were classified into three types according to the similarities in hydrophobicity and in structure. Except for urea, formamide and dimethylsulfoxide, there was found a correlation between the ORD and the adsorption data. Alcohols were considered to give effect selectively on the indole group of L-tryptophan, while glycols to give effect also on the moiety other than the indole group. Urea and formamide might give effect on the hydrophilic moiety of L-tryptophan to result in the decrease in optical rotation, but this effect was considered to have no relation to the increase in solubility. Analyzing the relationship between the ORD and the adsorption data, the present 3rd components were classified into three types, corresponding to the previous classification according to solubility studies. Finally, the results verified the concept regarding the contact of 3rd component with L-tryptophan to result in the increase in solubility in aqueous solution.
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HIROAKI NANBA, HISATORA KURODA
1971 Volume 19 Issue 3 Pages
448-452
Published: March 25, 1971
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The chemical structure of the polysaccharide, a main component of cell walls of Cochliobolus miyabeanus, was studied. The polysaccharide, isolated from the fungal cell walls, was methylated by Hakomori's method and, after hydrolysis, the products were determined by paper chromatography, thin-layer chromatography, gas-liquid chromatography and paper electrophoretic chromatography. The molar ratio of the determined methyl sugars in the hydrolysate was as follows : 2, 3, 4, 6-tetramethyl- : 2, 4, 6-trimethyl- : dimethyl- (probably 2, 4-dimethyl-) glucose=3 : 10 : 2. These results demonstrated that the polysaccharide in this fungal cell wall is composed of the β-1, 3 linked glucan having branched units connected through C-6 and C-1.
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HIKOKICHI OURA, SUSUMU HIAI, SHOICHI NAKASHIMA, KINJI TSUKADA
1971 Volume 19 Issue 3 Pages
453-459
Published: March 25, 1971
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The in vivo administration of extract of the roots of Panax ginseng C. A. MEYER increased the incorporation rate of labeled precursors into liver nuclear RNA at 4 hr and into cytoplasmic polysomal RNA at 5.5-6.0 hr after a single dose intraperitoneal injection in a rat. The incorporation rate was directly dependent on the amount of a fraction obtained by partial purification. The increased specific radioactivity of the liver RNA is not due to the change in the pool size of endogenous acid-soluble nucleotides.
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NOBORU NAKAI, JUNICHI HASE
1971 Volume 19 Issue 3 Pages
460-467
Published: March 25, 1971
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1. 2-Methyl-1, 4-naphthoquinone (K
3) reacted with sulfhydryl groups of yeast alcohol dehydrogenase to form a thioehter linkage at 3-position of the quinone with absorption maximum at 430 mμ, as well as with sulfhydryl groups of low molecular compounds, bovine serum albumin and papain. 2. Under the reaction conditions at 0°, K
3 preferentially combined with essential sulfhydryl groups of the enzyme without any change in its conformation such as dissociation into subunits. 3. From the tryptic digest of the <
14>C labeled K
3 bound yeast alcohol dehydrogenase, a radioactive peptide consisted of 37 amino acid residues was isolated.
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TAKATSUKA YASHIKI, TAI MATSUZAWA, TAKAO KONDO, YOSHIAKI UDA, TAKASHI S ...
1971 Volume 19 Issue 3 Pages
468-477
Published: March 25, 1971
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Urinary metabolites of a non-steroidal anti-inflammatory drug, 5-n-butyl-1-cyclohexyl-2, 4, 6-trioxoperhydropyrimidine (BCP) were investigated in man. Tow hydroxylated compounds, 1-cyclohexyl-5-(3-hydroxybutyl)-2, 4, 6-trioxoperhydropyrimidine (II) and 5-n-butyl-1-(4-hydroxycyclohexyl)-2, 4, 6-trioxoperhydropyrimidine (IV) were identified as the metabolites besides unchanged BCP, though two unknown minor peaks were observed by gas-liquid chromatography. The glucuronides or sulfates of II and IV were not detected clearly.
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TAKATSUKA YASHIKI, TAKAO KONDO, YOSHIAKI UDA, HIROYUKI MIMA
1971 Volume 19 Issue 3 Pages
478-486
Published: March 25, 1971
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The determination-procedures of BCP and its urinary metabolites, 1-cyclohexyl-5-(3-hydroxybutyl)-2, 4, 6-trioxoperhydropyrimidine (II) and 5-n-butyl-1-(4-hydroxycyclohexyl)-2, 4, 6-trioxoperhydropyrimidine (IV) were investigated by ultraviolet absorption method. Total and free BCP in a urine were determined separately by changing the conditions for extraction. The metabolite II in a urine was determined selectively by converting it to 3-cyclohexyl-7-methyl-1, 2, 3, 4, 6, 7-hexahydro-5-H-pyrano (2, 3-d) pyrimidine-2, 4-dione (XV), though IV was not determined by this method as the separation from the unknown metabolites was not successful.
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TAKATSUKA YASHIKI, YOSHIAKI UDA, TAKAO KONDO, HIROYUKI MIMA
1971 Volume 19 Issue 3 Pages
487-492
Published: March 25, 1971
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An investigation was carried out on the gas-liquid chromatographic determination of 5-n-butyl-1-cyclohexgl-2, 4, 6-trioxoperhydropyrimidine (BCP) and its metabolites, i.e., 1-cyclohexyl-5-(3-hydroxybutyl)-2, 4, 6-trioxoperhydropyrimidine (II) and 5-n-butyl-1-(4-hydroxycyclohexyl)-2, 4, 6-trioxoperhydropyrimidine (IV) in human urines. Neopentyl glycol succinate (NGS) 2% on Gas Chrom P was selected as the liquid stationary phase and a hydrogen flame ionization detector was employed. By trimethylsilylation of the chloroform extract from a urine, BCP and IV were determined simultaneously with phenobarbital as the internal standard, for IV was subjected trimethylsilylation, while BCP was not affected by the treatment. The metabolite II was determined selectively by heating it in an acid medium to convert into 3-cyclohexyl-7-methyl-1, 2, 3, 4, 6, 7-hexahydro-5-H-pyrano (2, 3-d) pyrimidine-2, 4-dione (XV). Cyclobarbital or phenylbutazone was used as the internal standard in this case.
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MINEO SANEYOSHI
1971 Volume 19 Issue 3 Pages
493-498
Published: March 25, 1971
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Direct and simple methods for the preparations of 4-thiouridine 5'-phosphate (IVa), 6-thioinosine 5'-phosphate (IVb) and 6-thioguanosine 5'-phosphate (IVc) from the corresponding oxy-nucleotides are described. The 5'-ribonucleotides are converted to their 2', 3'-di-O-acetylated derivatives by a conventional acetylation procedure, followed by thiation with phosphorus pentasulfide to give crude thiated products. For the selective desulfurization, the crude products are treated with dicyclohexylcarbodiimide, followed by alkaline deacylation to give the desired "thio" nucleotides.
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YOSHIO MORI, MIHARU NAKAMURA
1971 Volume 19 Issue 3 Pages
499-504
Published: March 25, 1971
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Kovats indices of 18 furanosesquiterpenoids on 8 columns were calculated. The additivity rule for substituent index was found to be valid. Using this rule, a tentative identification of substituents was discussed.
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KIYOSHI ISONO, TSUNEMASA AZUMA, SABURO SUZUKI
1971 Volume 19 Issue 3 Pages
505-512
Published: March 25, 1971
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5'-δ-Carbamoyloxy-L-x-aminovaleramido-5'-deoxyuridine, a polyoxin analog, was prepared by the reaction of 5'-amino-5'-deoxy-2', 3'-O-isopropylideneuridine and N-carbobenzoxy-L-α-aminovalero-δ-lactone, followed by carbamoylation and the removal of the protective groups. Several other ω-substituted aminoacyl derivatives were also prepared utilizing the activated ester method and the mixed anhydride method. All these compounds showed no polyoxin-activity.
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HIDEYO SHINDO, ISAO TAKAHASHI, EIICHI NAKAJIMA
1971 Volume 19 Issue 3 Pages
513-522
Published: March 25, 1971
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The distribution of
14C-anisotropine methbromide, a quaternary ammonium derivative of atropine, was studied in mice by whole-body autoradiographic technique. After i. p. and s. c. injections, the radioactivity was found to be mainly concentrated in the excretory organs : the liver, kidney, gall and urinary bladders, gastrointestinal tract and salivary gland, indicating a rapid excertion of the drug via both the urinary and biliary routes. In addition, the radioactivity was found to be accumulated specifically in the pancreas, gastric mucosa, walls of the spermatic and oviducts and uterus. Almost no accumulation was observed in the central nervous system, the muscular tissues and the endocrine organs. Autoradiography in mice of which the common bile duct was ligated prior to the injection showed an occurrence of a glandular secretion of the drug into the intestinal mucosa from the blood circulation. After oral administration, the radioactivity was found to be restricted very effectively to the gastrointestinal tract, indicating a limited absorption from the intestine, and the most part of the absorbed drug to be cleared back into the intestinal tract via the bile. These characteristics are discussed with respect to the structural characteristic of quaternary ammonium structure and the possible relations are pointed out between the sites of the drug accumulation and those of the pharmacological action where the drug has been clinically applied as a peripheral anti-spasmodic agent with a lower side effect than has atropine.
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YASUMITSU TAMURA, YASUYUKI KITA, YOSHIKO MATSUTAKA, MASANAO TERASHIMA
1971 Volume 19 Issue 3 Pages
523-528
Published: March 25, 1971
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The synthetic methods for 3-alkoxy- (IIa, b, c and IIIa, b, c) and hydroxy-2-cyclohexen-1-one oximes (IVa, c) were established. Treatment of dihydroresorcinol (Ia), dihydroorcinol (Ib), dimedone (Ic) and their derivatives with hydroxylamine hydrochloride in methanol, ethanol and water afforded good yields of IIa, b, c, IIIa, b, c and IVa, c. The reaction mechanisms and configurations of the oximes are also mentioned. Inaddition, our experiments revealed that the Gittel's assignment on the product obtained the bytreatment of dimedone (Ic) and NH
2OH·HCl in ethanol was erronous, that is, the product was not 3-hydroxy-5, 5-dimethyl-2-cyclohexen-1-one oxime (IVc) assigned by him, but 3-ethoxy-5, 5-dimethyl-2-cyclohexen-1-one oxime (IIIc).
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ZENICHI HORII, KAZUO OHKAWA, SANGWON KIM, TAKEFUMI MOMOSE
1971 Volume 19 Issue 3 Pages
535-537
Published: March 25, 1971
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The structure of diphyllin or justicidin A was discussed from nuclear magnetic resonance (NMR) spectral evidences and concluded to be II or IX on the basis of its synthesis.
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MORIO IKEHARA, YUJI NAKAHARA, SHOJI YAMADA
1971 Volume 19 Issue 3 Pages
538-544
Published: March 25, 1971
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N
6-Benzoyladenine (II) and 1, 2, 3, 5-tetraacetyl-D-xylofuranose (I) were condensed by fusion method to obtaine α- and β-D-xylofuranosyladenine (IV). Though the β-nucleoside was obtained in a pure crystalline form, the α-anomer was obtained as crystals containing 27% β-anomer as measured by nuclear magnetic resonance. β-D-Xylofuranosyladenine (IVa) was brominated at 8-position and then derived to 3', 5'-O-isopropylidene derivative (VI). Tosylation of VI at 2'-OH followed by the treatment with 40% aqueous NaSH gave a cyclonucleoside, 8, 2'-anhydro-8-mercapto-3', 5'-O-isopropylidene-β-D-xylofurnaosyladenine (VII). De-sulfurization with Raney nickel and deprotection with acid gave a novel nucleoside, 9-β-(2-deoxy-threo-D-pentofuranosyl) adenine (X). From α-D-xylofuranosyladenine (IVb), bromination at 8-position with brominewater in pH 4 gave a crystalline cyclonucleoside, 8, 2'-anhydro-8-oxy-9-α-D-xylofuranosyladenine (XV). Optical rotatory dispersion spectrum of XV showed a large negative Cotton effect in contrary to the β-cyclonucleoside, which had the positive effect in B-band region.
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SADAO OHKI, TATSUO NAGASAKA
1971 Volume 19 Issue 3 Pages
545-551
Published: March 25, 1971
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1-Acetyltryptophan and its derivatives were synthesized in good yields from dltryptophan. Reduced nucleophilic activity in the indole ring by 1-acetylation was examined in the reaction of 1-acetyl derivatives with o-nitrophenylsulfenyl chloride (NPS-Cl) and the Friedel-Crafts reaction of them. In the reaction with NPS-Cl, 7, 10, and 12 did not show the activity of 2-position in the indole ring, but the Friedel-Crafts reaction of 12 (chloride) afforded 15 cyclized to 2-position of the indole, different from only one example reported previously by Szmuszkovicz of the same reaction of 1-acetyl indole derivatives which cyclized to 4-position.
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HARUO KITAGAWA, KYOICHI HIGO, TAKESHI NARUKE, TSUTOMU IRIKURA
1971 Volume 19 Issue 3 Pages
552-558
Published: March 25, 1971
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K-31, a proved hypocholesterolemic agent, was studied about its effect on the metabolism as well as biosynthesis of cholesterol in rats using
14C-labeled cholesterol and acetate. K-31 increased the recoveries of
14C in the 2nd day's bile and feces in rats injected [4-
14C] cholesterol. Addition of K-31 as hydrochloric acid salt solution to the liver homogenates from normal rats did not affect the incorporation of [1-
14C] acetate into cholesterol. However, increased cholesterogenesis was observed in the liver homogenates from rats fed 0.5% K-31 in diet for 21 days. K-31 significantly enhanced hepatic cholesterogenesis in intact rats. Increased hepaticcholesterogenesis restored to control levels by the withdrawal of the feeding of K-31. Thus, the hypocholesterolemic action of K-31 was considered to depend on the inhibition of the intestinal cholesterol absorption with increasing excretion of cholestrol into bile and feces.
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KATSUTADA MASUDA, TAKAAKI KAMIYA, KENICHI KASHIWA
1971 Volume 19 Issue 3 Pages
559-563
Published: March 25, 1971
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Several hitherto unknown mesoionic compounds, Ψ-3-aryl-5-imino-3, 5-dihydro-1-oxa-2, 3, 4-triazole hydrochlorides (III) were synthesized starting from monoarylhydrazines (IV) via cyanohydrazines (V) and nitrosocyanohydrazines (VI). The mesoionic compounds (III) were converted into their N-acyl derivatives (VIII) by treatment with various acylating agents. The free base (VII) was isolated in crystalline from the 3-phenyl homolog of III by treatment with aqueous bicarbonate ; although the corresponding sydnonimine hydrochloride has been known to result in the ring opening under similar conditions.
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KAZUYOSHI IKEDA, YOSHIHISA MIZUNO
1971 Volume 19 Issue 3 Pages
564-570
Published: March 25, 1971
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Structures of Levene's 5-phenylhydrazinouracil derivatives (VIII) and 5, 6-diphenyl-hydrazinouridine (III) formed by reactions of 5-hydroxyuracil derivatives and brominated uridine with phenylhydrazine, were revised to 5-oxo-5, 6-dihydrouracil phenylhydrazone derivatives (XI) and 5-oxo-6-phenylhydrazino-5, 6-dihydrouridine phenylhydrazone (IIa), respectively, by means of physical analyses. These resolutions were substantiated by the separation of optical active isomers of compound IIa and by proving the existence of syn- and anti-isomers with the compounds of XI type, except 5-oxo-5, 6-dihydrouridine phenylhydrazone (VII).
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YASUMITSU TAMURA, YASUYUKI KITA, MASAYUKI SHIMAGAKI, MASANAO TERASHIMA
1971 Volume 19 Issue 3 Pages
571-575
Published: March 25, 1971
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Heating of 3-allyloxy-2-cyclohexen-1-ones (IIa, b, c) caused a Claisen rearrangement and simultaneous cyclization to give 2-methyl-4-oxo-2, 3, 4, 5, 6, 7-hexahydrobenzofurans (IIIa, b, c) in 75, 70 and 78% yields, respectively. Under similar conditions, 3-allyloxy-2-methyl-2-cyclohexen-1-one (VI) gave 2-allyl-2-methylcyclohexane-1, 3-dione (VII) in 81% yield, and 3-prenyloxy-2-cyclohexen-1-one (VIII) gave 2, 2, 3-trimethyl-4-oxo-2, 3, 4, 5, 6, 7-hexahydrobenzofuran (IX) in 95% yield. The reaction mechanisms were also discussed.
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KINICHI IMAI, RYUJI MARUMOTO, KUNIO KOBAYASHI, YOSHIO YOSHIOKA, JUN TO ...
1971 Volume 19 Issue 3 Pages
576-586
Published: March 25, 1971
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Ring closure of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside) with phenyl isothiocyanate afforded 2-mercaptoinosine (I) in good yield. Similarly, the ring closure of AICA-riboside 5'-phosphate (AICAR) led to the formation of 2-mercaptoinosine 5'-phosphate (II). Various 2-substituted inosine 5'-phosphates were prepared from I and II or starting with AICA-riboside. It was found that 2-furfuryl-thioinosine 5'-phosphate possessed a flavor enhancing activity of about 17-times that of inosine 5'-phosphate. The chemical structure-flavor enhancing activity relationship was presented.
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HIROYUKI INOUYE, SHINICHI UEDA, YOSHIO TAKEDA
1971 Volume 19 Issue 3 Pages
587-594
Published: March 25, 1971
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Feeding of [10
14-C]-sweroside (I), prepared by the route shown in Chart 1, to plants established that this glucoside (I) was incorporated into gentiopicroside (III) and vindoline (VI). Substance I was also incorporated into reserpinine (VII) and quinine (V). These data confirmed the biosynthetic sequence of the gentianaceous secoiridoid glucosides and the biological conversion of sweroside (I) to Vinca and Cinchona alkaloids.
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HIROSHI KUGITA, HIROZUMI INOUE, MUNEYOSHI IKEZAKI, MIKIHIKO KONDA, SAT ...
1971 Volume 19 Issue 3 Pages
595-602
Published: March 25, 1971
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Various derivatives of 2-aryl-3-hydroxy-2, 3-dihydro-1, 5-benzothiazepin-4 (5H)-one (I) were synthesized. Alternative routes to 2-aryl-3-hydroxy-5-alkyl-trans-2, 3-dihydro-1, 5-benzothiazepin-4 (5H)-one (II-β) and 2-aryl-3-acetoxy-5-dimethylaminoethyl-cis-2, 3-dihydro-1, 5-benzothiazepin-4 (5H)-one (VI-α) were also investigated respectively.
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TATSUO NAGASAKA, SADAO OHKI
1971 Volume 19 Issue 3 Pages
603-611
Published: March 25, 1971
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Oxidation of N-phthaloyl-1-acetyltryptophan (1) with chromium trioxide afforded the kynurenine derivative (4) in 35% yield and the dioxindole lactone (6) in 20% yield. The latter substance was separated into the two epimers (6a and 6b) and their configura tion was examined. N-Bromosuccinimide (NBS) in tert-butanol converted N-phthaloyltryptophan (7) to the corresponding oxindole (9) in 51% yield when a 1 : 1 mole ratio of NBS to indole was used. When a 2 : 1 ratio of reactants was used and its products were treated with sodium hydrogen carbonate, the dioxindole lactone (8) was obtained, and acetylation of 8 afforded 6 that agreed with the oxidation product. The mass spectra of 8 and 9 are discussed.
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TOSHIO NAMBARA, HIROSHI HOSODA, MASAHIRO USUI, TAKAKO ANJYO
1971 Volume 19 Issue 3 Pages
612-616
Published: March 25, 1971
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3β-Acetoxy-17β-bromo-5α, 14β-androstan-16-one (VII) was synthesized by two different routes, namely from the Δ
16-ene (VIII) through the 16, 17-bromohydrin (IX) and from the 16-ketone (V) as shown in Chart 1. The epimeric 17α-bromo compound (X) was pre-pared from VII upon treatment with hydrobromic acid. On the basis of infrared, rotatory dispersion and circular dichroism spectral and polarographic data the nature of C-bromine bonds and the conformation of ring D with a ketone at C-16 have been discussed. A new method for synthesis of the 17α-hydroxy-16-ketone (IV) from the 17-ketone (I) is also described.
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ISAO ISHIGURO, RIKIO SHINOHARA
1971 Volume 19 Issue 3 Pages
617-623
Published: March 25, 1971
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Examination of the effect of reductants on hematin, which is a prosthetic group of tryptophan oxygenase, showed that glutathione and cysteine changed the optical absorption of hematin and, therefore, the effect of these reductants on tryptophan oxygenase activity was studied. Glutathione and cysteine are both SH-compounds, but their effect on tryptophan oxygenase activity is quite different. Glutathione in 0.1-0.2 mM concentration inhibited tryptophan oxygenase activity, but more than 0.1-0.2 mM of glutathione resulted in recovery of inhibition of tryptophan oxygenase activity, which was activated by 5.0 mM glutathione. On the other hand, cysteine activated tryptophan oxygenase maximally in 0.1-0.2 mM concentration, but more than 0.1-0.2 mM of cysteine rapidly decreased its maximum activity. The inhibition rate of tryptophan oxygenase activity by these reductants was decreased by the addition of purified rat liver catalase.
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YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, SHIGERU TAGUCHI
1971 Volume 19 Issue 3 Pages
624-627
Published: March 25, 1971
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In the studies of alcoholyses of (trifluoromethyl) quinolines, 3-(trifluoromethyl) compounds (II and V) were found to be more reactive to nucleophile than other isomers (I, III, IV, and VI), which were more reactive than benzotrifluoride, in turn. Two different mechanisms are proposed for each process. Reduction of N-oxide groups with sodium alkoxides are also reported.
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MASATO ASAHINA, TSUTOMU YAMAHA, KUNIKO WATANABE, GUINETTE SARRAZIN
1971 Volume 19 Issue 3 Pages
628-632
Published: March 25, 1971
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SHIGERU GOTO, TAKAYUKI TOI
1971 Volume 19 Issue 3 Pages
632-637
Published: March 25, 1971
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HITOSHI MINATO, REIKO FUJIOKA, KENICHI TAKEDA
1971 Volume 19 Issue 3 Pages
638-640
Published: March 25, 1971
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KIYOSHI HATA, MITSUGI KOZAWA, KIMIYE BABA, KUNYING YEN
1971 Volume 19 Issue 3 Pages
640-642
Published: March 25, 1971
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TOYOSHIGE KABEYA, KAZUYA KOHASHI, YOSUKE OHKURA, TSUTOMU MOMOSE
1971 Volume 19 Issue 3 Pages
645-646
Published: March 25, 1971
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SHUNSAKU NOGUCHI, SHOJI KISHIMOTO, ISAO MINAMIDA, MIKIHIKO OBAYASHI, K ...
1971 Volume 19 Issue 3 Pages
646-648
Published: March 25, 1971
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