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Volume 32, Issue 3
Displaying 1-50 of 69 articles from this issue
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HIROFUMI TAKEUCHI, YOSHIHISA MIWA, SHUSHI MORITA, JUTARO OKADA1984 Volume 32 Issue 3 Pages 823-831
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe catalytic activities of eight different types of triphase catalyst (immobilized phase transfer catalyst) were examined in the displacement reaction of several anions with benzyl bromide and n-octyl methanesulfonate at 70 and 90°C, respectively. The catalysts were prepared by the reaction of 1% cross-linked chloromethylated polystyrene with such tertiary amines as R3N (R=ethyl, n-propyl, n-butyl) and R (CH3)2N (R=ethyl, n-butyl, n-dodecyl, n-hexadecyl) and trin-butylphosphine. The catalytic activity for the reaction of n-octyl methanesulfonate increased with increasing size of the immobilized quaternary cation. The catalysts with bulky cations having different central atoms ([resin]-CH2N+(C4H9)3, [resin]-CH2P+(C4H9)3) showed almost the same catalytic activity in every reaction tested. Variation of the structure of the immobilized cation was concluded to modify the catalytic activity not only by changing the anion-cation interaction energy but also by changing the reaction environment around the active site.View full abstractDownload PDF (809K) -
MIYOKO SUZUKI, YOSHIO SASAKI1984 Volume 32 Issue 3 Pages 832-838
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe behavior of orange II-γ-cyclodextrin (cdx) complex was examined in the solution state. 1H-Nuclear magnetic resonance (NMR) data indicate that orange II can pass through γ-cdx. The molar ratios of orange II : γ-cdx as determined from Job plots was 1 : 1 (13C-NMR) and 2 : 1 (1H-NMR). Simulation of the equilibrium constants (K)'s was attempted with three systems. K's of the complex determined by the C-SO-3 at 66°C could be well represented by an A+B=AB, AB+B=AB2 system and gave K1=74, K2=5, indicating the coexistence of 1 : 1 and 2 : 1 complexes. On the other hand, β-cdx complex showed a 1 : 1 ratio in Job plots of both 1H and 13C data, giving K1=2370 in an A+B=AB system, no improvement was obtained by applying an A+B=AB, AB+B=AB2 system. Generally, the 13C-NMR signals of γ-cdx-induced orange II show high-field shifts compared to those of the β-cdx complex. This may be due to the superiority of the hydrophobic interaction to other factors. Judging from the circular dichroism (CD) spectra, γ-and β-cdx include orange II in different directions and there is no electrostatic interaction between γ-cdx and orange II.View full abstractDownload PDF (587K) -
KIYOKO TAKAMURA, SATOSHI INOUE, FUMIYO KUSU, MASAKI OTAGIRI, KANETO UE ...1984 Volume 32 Issue 3 Pages 839-845
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe electrochemical oxidation of a chlorpromazine (CPZ)-cyclodextrin (CyD) inclusion complex was studied in phosphate buffers by means of cyclic voltammetry. The voltammogram of the CPZ-CyD system exhibits three oxidation waves. The first wave, which is due to the oxidation of CPZ to form its cation radical, is catalytic in nature, and its peak current depends on pH and on the buffer concentration. The second wave is attributed to the oxidation of CPZ cation radical-phosphate adduct. The third wave appears to be the result of further oxidation of CPZ sulfoxide-CyD complex. The formation of an inclusion complex of CPZ with CyD leads to a lowering of the peak current of the first wave and a shift in the peak potential to the positive side at the same time. The presence of CyD exerts no appreciable effect on the second wave, suggesting a minor interaction between the radical and CyD, and this is consistent with the absorption, circular dichroism, and 1H-nuclear magnetic resonance (NMR) spectra. Based on these results, an electrochemical reaction mechanism for CPZ-CyD system is proposed.View full abstractDownload PDF (636K) -
YOHMEI OKUNO, OSAMU YONEMITSU1984 Volume 32 Issue 3 Pages 846-850
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new system containing Ru (bpy)3Cl2 and (Et4N)2 [Fe4S4 (SBzl)4] as a photocatalyst and a relay compound, respectively, was developed for hydrogen production from water by visible light irradiation. Studies on the effect of donors on the system clearly showed that EDTA was the most efficient among those investigated, and the hydrogen formation yields reached over 20000% with respect to both the photosensitizer and the iron-sulfur cluster. An interesting feature of the present system is the successful use of a ferredoxin model compound as a catalytic electron carrier.View full abstractDownload PDF (564K) -
YOSHIHARU SAKUMA, TOMOHISA NAGAMATSU, YUKO HASHIGUCHI, FUMIO YONEDA1984 Volume 32 Issue 3 Pages 851-859
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3, 4-Disubstituted 1-methylpyrimido [4, 5-c] pyridazine-5, 7 (1H, 6H)-diones (3, 4-disubstituted 4-deazatoxoflavins) and their analogues (II) were synthesized by the condensation of 6-(1-methylhydrazino) uracil derivatives (I) and appropriate α-diketones. Reduction of II with sodium dithionite in aqueous ammonia gave the corresponding 3, 4-disubstituted 4, 8-dihydro-4-deazatoxoflavins (III). Ethylation of IIf with ethyl iodide yielded the corresponding 3, 4-disubstituted 6-ethyl-4-deazatoxoflavin (VI). Treatment of IIh with chloromethylated polystyrene and potassium carbonate in dimethylformamide (DMF) gave the corresponding 3, 4-disubstituted 4-deazatoxoflavin resin (VII). The reaction of II with m-chloroperbenzoic acid in chloroform gave the corresponding 3, 4-disubstituted 4, 4a-epoxy-4-deazatoxoflavins (IV). Treatment of IV with 10% aqueous sodium carbonate resulted in the formation of oxazolonopyridazine derivatives (V). The oxidizing abilities of II, VI, and VII toward amines were examined to explore the usefulness of these compounds as oxidation-reduction catalysis. These compounds (II, VI, and VII) oxidized long-chain alkylamines such as n-octylamine, n-dodecylamine besides benzylamine and cyclohexylamine to yield the corresponding carbonyl compounds (via imines) catalytically with a remarkably high turnover number.View full abstractDownload PDF (864K) -
SUSUMU KITANAKA, MICHIO TAKIDO1984 Volume 32 Issue 3 Pages 860-864
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new anthraquinones, 1-desmethylchryso-obtusin (4), 1-desmethylobtusin (5) and 1-desmethylaurantio-obtusin (6), were isolated along with chrysophanol-10, 10'-bianthrone, questin and benzoic acid from the seeds of Cassia obtusifolia LINN., and their structures were established on the basis of spectral and chemical evidence.View full abstractDownload PDF (560K) -
MASUO MORISAKI, NOBUO IKEKAWA1984 Volume 32 Issue 3 Pages 865-871
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe high pressure liquid chromatographic behavior of forty sterol benzoates on a Zorbax ODS reverse phase column and on a normal phase column of Zorbax SIL is described.View full abstractDownload PDF (682K) -
SUSUMU TAKADA, YASUO MAKISUMI1984 Volume 32 Issue 3 Pages 872-876
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel and simple methods for preparing 4-aminomethyl-2, 3, 4, 9-tetrahydrothiopyrano [2, 3-b] indoles are described. Both involve thio-Claisen rearrangements of indol-2-yl propargyl sulfides as a key step which affords thiopyrano [2, 3-b] indoles in good yields. Elaboration of these compounds led to fused tryptamine analogues which were found to have strong analgesic activity. The mechanism of this novel rearrangement is discussed.View full abstractDownload PDF (656K) -
SUSUMU TAKADA, NATSUKI ISHIZUKA, TAKASHI SASATANI, YASUO MAKISUMI, HIR ...1984 Volume 32 Issue 3 Pages 877-886
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 4-aminomethyl-2, 3, 4, 9-tetrahydrothiopyrano [2, 3-b] indole derivatives was synthesized and evaluated for analgesic activity. Preliminary structure-activity relationship analysis showed that substitution on the benzene portion of the indole ring reduced the analgesic activity, whereas a short-chain Nb-alkyl substituent enhanced the potency, as exemplified by an Nb-methyl substituted analogue. This compound was equipotent to morphine in the acetic acid writhing assay using mice.View full abstractDownload PDF (788K) -
MASAHITO OCHIAI, EIICHI FUJITA, MASAO ARIMOTO, HIDEO YAMAGUCHI1984 Volume 32 Issue 3 Pages 887-890
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new general method for the synthesis of allyl nitrates is described. Allylmetal (group IVb) compounds, on treatment with thallium (III) nitrate in dioxane, gave the corresponding allyl nitrates in good yields.View full abstractDownload PDF (480K) -
YASUMITSU TAMURA, JUNICHI UENISHI, HIROYUKI ISHIBASHI1984 Volume 32 Issue 3 Pages 891-897
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkylation of the carbanions derived from six-membered β-ketosulfoxides, 3-methylisothiochroman-4-one 2-oxide (1) and 2-methylthian-3-one 1-oxide (8), with alkyl halide was found to occur trans to the S-O bond with high stereoselectivity. The mechanism of the stereoselective alkylation is discussed.View full abstractDownload PDF (675K) -
YASUMITSU TAMURA, JUNICHI UENISHI, HIROYUKI ISHIBASHI1984 Volume 32 Issue 3 Pages 898-901
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkylation of the carbanion derived from 2-methylbenzo [b] thiophen-3 (2H)-one 1-oxide (3) with alkyl halide was found to occur cis to the S-O bond with high stereoselectivity. A pyramidal structure is proposed for the intermediary carbanion based on the results of carbon-13 nuclear magnetic resonance spectroscopy.View full abstractDownload PDF (491K) -
JEAN-CHARLES LANCELOT, HENRIETTE LANDELLE, MAX ROBBA1984 Volume 32 Issue 3 Pages 902-908
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe acid anhydrides (5-7) were obtained by treatment of the corresponding 2, 3-carbazoledicarboxylic acids (2-4) with acetic anhydride. Friedel-Crafts reaction of these anhydrides with benzene or toluene gave either 3-aroylcarbazole-2-carboxylic acids (8-11) or 6, 7-phtaloylcar bazole (19-21) according to the reaction conditions. Treatment of the acids (8-11) with hydrazine hydrate gave 3, 4-dihydro-4-oxo-pyridazino [4, 5-b] carbazoles (14-17). When the anhydrides (5-7) were treated with hydrazine hydrate, the 1, 2, 3, 4-tetrahydropyridazino [4, 5-b]-carbazoles (26-28) were obtained. LiAlH4 reduction of a diester (1) gave the corresponding 2, 3-dihydroxymethyl derivative (23). When the latter compound was oxydized, the corresponding lactone (25) was resulted. The structure of all compounds was elucidated by means of elemental analyses, infrared (IR) and nuclear magnetic resonance (NMR) spectra.View full abstractDownload PDF (751K) -
HIROKO YAMAGUCHI, MASAYUKI ONDA1984 Volume 32 Issue 3 Pages 909-912
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of 4-methyl-1-oxoanhydroberberine (9) in the presence of nitrosobenzene gives two isomeric photoadducts (11) and (12). In the presence of diethyl azodicarboxylate, 9 affords two different types of photoadduct (13) and (14). These photoadducts are considered to be formed by the photochemically allowed [2s+2s+2+s] cycloaddition reactions.View full abstractDownload PDF (501K) -
SHIGEO AMEMIYA, KOICHI KOJIMA, KIYOSHI SAKAI1984 Volume 32 Issue 3 Pages 913-921
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethylenomycin A (3a) was converted to 10α, 11β-dimethyl-prostaglandin E2 (PGE2) (23), -PGF2α (27), -PGF2β (28) and -PGA2 (29).View full abstractDownload PDF (1107K) -
KOZO SHISHIDO, SHINICHI SHIMADA, KEIICHIRO FUKUMOTO, TETSUJI KAMETANI1984 Volume 32 Issue 3 Pages 922-929
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESScis-9b-Cyano-3a-methyl-2, 3, 3a, 4, 5, 9b-hexahydro-1H-benz [e] indene derivatives (14, 20) were synthesized stereoselectively via the intramolecular Diels-Alder reaction of 1, 2-dihydrobenzocyclobutenes (11, 19). The cis stereochemistry in the cycloadducts was confirmed by nuclear Overhauser effect (NOE) experiments. Examination of CPK molecular models revealed that the stereoselectivity of the transformations could be attributed to a predominance of the endo conformer (e.g. 12) in the transition state. Moreover, the stereochemical outcome of the decyanation of 14 by dissolving metal reduction is also considered.View full abstractDownload PDF (705K) -
KAZUO OGAWA, TADAFUMI TERADA, TAKAJI HONNA1984 Volume 32 Issue 3 Pages 930-939
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a part of our search for new potent analgesic agents, novel fused pyrazole derivatives were synthesized. The reaction of 2-substituted-5-hydroxypyrazole (I) with ethyl 2-substituted (for example COCH3 or CO2C2H5) acylacetates (II) gave mainly pyrazolo [1, 2-a] pyrazole-1, 5 (1H, 5H)-diones (III). On the other hand, similar reaction of I with diethyl benzoylmalonate gave mainly pyrazolo [5, 1-b] [1, 3] oxazin-5 (5H)-one (V) but did not give III at all. Thermal and photochemical isomerization of III gave V. Methanolysis of IIIa in the presence of LiOH occurred with retention of the 4-ethoxycarbonyl-5-pyrazolone ring and similar products (VIa and VIf) were obtained by methanolysis of Va and Vf, respectively. Analgesic activities of the present new compounds were all inferior to that of aminopyrine.View full abstractDownload PDF (986K) -
MASAICHIRO MASUI, YOSHIYUKI KAMADA, HIDEKO NISHIDA, SHIGEKO OZAKI1984 Volume 32 Issue 3 Pages 940-944
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnodic oxidation of ethylenediamines (ethane-1, 2-diamines) was investigated by cyclic voltammetry and controlled potential electrolysis in aqueous carbonate buffer (pH 10) at a glassycarbon electrode. The first wave of the diamines is developed at a lower potential than that of the corresponding β-alkanolamines. Among the oxidative bond cleavages, the relative amount of (α) C-(β) C bond fission is larger than that observed for β-alkanolamines and oxidative deamination is only observed after the (α) C-(β) C bond fission. A scheme for the reaction processes is proposed.View full abstractDownload PDF (530K) -
YASUMITSU TAMURA, JUNICHI UENISHI, HIROYUKI ISHIBASHI1984 Volume 32 Issue 3 Pages 945-949
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkylation of the 1, 3-dianion (2) of isothiochroman-4-one 2-oxide (1) with alkyl halide was shown to occur stereospecifically trans to the S-O bond at the C-1 position, whereas deuteration of the dianion with deuterium oxide at the same position occurred cis to the S-O bond.View full abstractDownload PDF (512K) -
MINORU MACHIDA, KAZUAKI ODA, YUICHI KANAOKA1984 Volume 32 Issue 3 Pages 950-956
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of N-[ω-(cycloalken-1-yl) alkyl] succinimides (9c-f) (m≨2) afforded mainly azepinediones (13c-f) with ring enlargement as the Norrish type II cyclization products. In the case of m=1, spiro-azepinedione derivatives (11a, b) were obtained in addition to tricyclic nitrogen heterocycles (10a, b), the Norrish type II products. These spiro-azepinediones are probably formed via imide-oxetanes by the intramolecular Paterno-Buchi reaction of these succinimides in competition with the type II processes.View full abstractDownload PDF (710K) -
YOSHIO ITOH, SETSUZO TEJIMA1984 Volume 32 Issue 3 Pages 957-966
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a preliminary experiment aimed ultimately at the total syntheses of high mannose-type oligosaccharides in glycoproteins, two fully acetylated tetrasaccharides, Manα1→2Manα1→3Manβ1→4GlcNAc (32) and Manα1→3Manα1→6Manβ1→4GlcNAc (35), were synthesized by block condensation of acetylated dimannopyranosyl bromides with suitably protected Manβ1→4GlcNAc derivatives by modified Koenigs-Knorr reactions, followed by acetylation of the deprotected tetrasaccharides. Proton and carbon-13 nuclear magnetic resonance spectral data for 32, 35, and synthetic intermediates are also presented. The present work confirms that 1, 6-anhydro-β-derivatives of GlcNAc and oligosaccharides are versatile starting materials or key intermediates for syntheses of complex oligosaccharides.View full abstractDownload PDF (1195K) -
SABURO SUGAI, HIROSHI IKAWA, YOSHIHIRO HASEGAWA, SEIICHIRO YOSHIDA, TE ...1984 Volume 32 Issue 3 Pages 967-976
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwenty-four derivatives (5) of 4-acyloxy-1-(1, 3-dioxolan-4-ylmethyl) piperidine were synthesized and their spasmolytic activities were examined. Some of them showed remarkable papaverine-like and/or atropine-like activities ; in particular, compounds 5c, 5d, 5e, 5l, and 5p were as active or more active than papaverine. The introduction of lipophilic substituents on the dioxolane moiety increased the papaverine-like activity.View full abstractDownload PDF (806K) -
SABURO SUGAI, YOSHIHIRO HASEGAWA, SEIICHIRO YOSHIDA, SANYA AKABOSHI1984 Volume 32 Issue 3 Pages 977-985
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSQuaternization of 4-acyloxy-1-(1, 3-dioxolan-4-ylmethyl) piperidine derivatives with methyl bromide afforded two diastereoisomers in equal amounts. The stereochemistry of these compounds was determined from the chemical shift of the N-methyl signals in the proton nuclear magnetic resonance (1H-NMR) spectra. The quaternary salts showed high anticholinergic activities. The trans isomers tended to be more potent than the corresponding cis isomers.View full abstractDownload PDF (874K) -
JUTARO OKADA, KOICHI NAKANO, MASAHARU SHIMABAYASHI, TORU MAEJIMA1984 Volume 32 Issue 3 Pages 986-994
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the purpose of increasing the analgesic activity of N-[1-methyl-2-(4-phenethyl-piperazino) ethyl] propionanilide (I), several substituent groups were introduced into both benzene rings of I. 1-[2-Methyl-2-(N-propionyl-p-or m-substituted-phenylamino) ethyl]-4-phenethylpiperazines (VIa-f, h) and 1-[2-methyl-2-(N-propionyl-p-methoxyphenylamino) ethyl]-4-(p-substituted-phenethyl) piperazines (XIIa-e) were prepared by substitution at the p-or m-position of the aniline moiety, and by substitution at the p-position of the phenethyl moiety, respectively. Potent activity (92-100% inhibition of writhing at 30mg/kg, s.c.) could be achieved by introducing alkoxyl groups into the benzene ring of the aniline moiety. Among such compounds, 1-[2-methyl-2-(N-propionyl-p-methoxyphenylamino) ethyl]-4-phenethylpiperazine (VIa) showed the highest activity (ED50 : 1.64mg/kg, s.c.). On the other hand, introduction of several substituents into the benzene ring of the phenethyl moiety resulted in low analgesic activities (2-58% inhibition of writhing at 30mg/kg, s.c.).View full abstractDownload PDF (862K) -
AKIRA SHIOZAWA, YUHICHIRO ICHIKAWA, MICHIO ISHIKAWA, YOSHIYA KOGO, SHU ...1984 Volume 32 Issue 3 Pages 995-1005
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA number of 6-substituted 5, 6, 7, 8-tetrahydro-1, 6-naphthyridines designed as cyclic homologues of betahistine, 2-(2-methylaminoethyl) pyridine, were synthesized by the reduction of the corresponding 1, 6-naphthyridinium salts. The antivertigo activity of these derivatives was evaluated in terms of their ability to inhibit spontaneous nystagmus in cats. The relationships between the molecular structures of the test compounds and their antivertigo activities were investigated by a regression analysis based on the lipophilicity (π) of the substituents at the 6-position and by a conformational analysis of the compounds of interest using the modified neglect of diatomic overlap molecular orbital method. Among these compounds, the 6-allyl-and 6-cyclopropylmethyl derivatives exhibited extremely potent activity with greatly reduced hypotensive action.View full abstractDownload PDF (984K) -
MUNEKAZU IINUMA, TOSHIYUKI TANAKA, SHIN MATSUURA1984 Volume 32 Issue 3 Pages 1006-1010
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSKanzakiflavone-1 and-2, isolates from Iris unguicularis, and their position isomers were synthesized to confirm the structures of the isolates. The differences among these flavones are discussed on the basis of spectral data.View full abstractDownload PDF (670K) -
SHIGERU YOSHIDA, KAYOKO ODA, SHINGO HIROSE1984 Volume 32 Issue 3 Pages 1011-1017
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn non-aqueous titration, the color shade at the equivalence point was decided graphically by utilizing complementary tristimulus colorimetry. It was also shown that the color shade at the equivalence point could be decided from the pKa value in aqueous solution of a weakly basic sample. Visual detection of the end-point in anhydrious acetic acid was possible when the sample concentration was higher than 10-2 M. A general expression for determination of the equivalence point is presented, and factors influencing the titration are discussed.View full abstractDownload PDF (663K) -
SHOICHIRO TAGAMI, YOSHIHIRO MURAMOTO1984 Volume 32 Issue 3 Pages 1018-1024
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple potentiometric method for the determination of chlorzoxazone, based on the use of a carbon dioxide gas-sensing electrode, is described. Details are also given of the operation and handling of the carbon dioxide electrode and the effects of factors which influence the potential. Chlorzoxazone decomposes into aminophenol and sodium carbonate on refluxing with 3N sodium hydroxide. After acidification with pH 4.5 citrate buffer, the carbon dioxide evolved in the decomposition solution was determined. A linear calibration plot was obtained within the concentration range of 3×10-4-5×10-3 M drug. The method was applied to the analysis of tablets.View full abstractDownload PDF (652K) -
TSUYOSHI TANIMOTO, HIDEO FUKUDA, JIRO KAWAMURA1984 Volume 32 Issue 3 Pages 1025-1031
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe properties of two aldose reductases (Ia and Ib) from rabbit lens were investigated. Both enzymes showed similar substrate specificity, and were capable of reducing various aldoses and aldehydes. On the basis of apparent Km, Vmax and second-order rate constant (kcat/Km) values, both enzymes had the highest reductive efficiency toward aromatic aldehydes such as pnitrobenzaldehyde. Among the aldoses tested, the aldose reductases exhibited a high affinity for DL-glyceraldehyde (Km of 31μM for Ia and 32μM for Ib) and a low affinity for D-glucose (Km of 92mM for Ia and 126mM for Ib). Aldose reductase I's could utilize both reduced nicotinamide adenine dinucleotide phosphate (NADPH) and reduced nicotinamide adenine dinucleotide (NADH) as coenzymes, but NADH was less effective than NADPH. The Km values for NADPH (1.4μM for Ia and 1.3μM for Ib) were much smaller than those for NADH (420μM for Ia and 270μM for Ib). Aldose reductase I's were strongly activated by sulfate ion and their Km and Vmax values for substrate and coenzyme were increased. Aldose reductase I's were inhibited strongly by aldose reductase inhibitors : about 80% by 0.3μM quercitrin, 65% by 1.6μM quercetin and about 70% by 8.0μM 3, 3-tetramethyleneglutaric acid. NADP+ and adenosine 2', 5'-diphosphate (2', 5'-ADP) were strong competitive inhibitors of both aldose reductase I's with respect to the coenzyme. The K1 values for 2', 5'-ADP were about 30μM, and those for NADP+ were about 70μM.View full abstractDownload PDF (739K) -
TSUYOSHI TANIMOTO, HIDEO FUKUDA, JIRO KAWAMURA, MASUMI NAKAO, UTAKO SH ...1984 Volume 32 Issue 3 Pages 1032-1039
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwenty kinds of oxazole derivatives having various substituents at the C-2 and C-5 positions were synthesized and tested in vitro for inhibition of rabbit lens aldose reductase (Ia and Ib), the enzyme that initiates cataract formation in diabetes. Compounds possessing bulky groups at C-2 and C-5 of the oxazole skeleton were found to be potent inhibitors. Benzyl 5-phenyl-2-oxazolecarbamate (12) inhibited aldose reductases Ia and Ib by 50% at about 15μM. N-Phenyl-N'-(5-phenyl-2-oxazolyl) urea also exhibited inhibitory activity comparable to that of compound 12. The structure-inhibitory activity relationships are discussed.View full abstractDownload PDF (650K) -
YORIHISA TANAKA, YUKO NISHIKAWA, KEIICHI MATSUDA, MITSUO YAMAZAKI, RYO ...1984 Volume 32 Issue 3 Pages 1040-1048
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe enzyme which catalyzes the reduction of the cyclopentanone moiety of sodium 2-[4-(2-oxocyclopentylmethyl) phenyl] propionate dihydrate (loxoprofen sodium) was purified from rabbit liver cytosol to homogeneity as judged by polyacrylamide gel electrophoresis. The purified enzyme had a molecular weight of 33000, showed a preference for nicotineamide adenine dinucleotide phosphate as a cofactor and had an optimal pH of 6.2. The Km and Vmax values for the reduction of loxoprofen were 0.45mM and 0.81 μmol/min/mg protein, and the trans-alcohol was the main product. The reducing activity was inhibited by p-chloromercuribenzoate, N-ethylmaleimide and quercitrin. The enzyme efficiently catalyzed reduction of various aromatic aldehydes and ketones, cyclohexanones and 5α-3-ketosteroids. Cyclopentanone and its methylsubstituted derivatives were not reduced at all. However, 2-ethyl-and 2-n-propylcyclopentanone were reduced, and 2-benzylcyclopentanone was a good substrate, comparable to loxoprofen itself. These results strongly suggest that the loxoprofen reducing enzyme is probably identical with the aromatic aldehyde-ketone reductase (F3) of rabbit liver cytosol, identified as 3α-hydroxysteroid dehydrogenase by Sawada et al.View full abstractDownload PDF (908K) -
YOICHI SAWAYANAGI, TAKASHI SONOBE, HIROITSU KAWATA, NAOKI NAMBU, TSUNE ...1984 Volume 32 Issue 3 Pages 1049-1054
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUsing buformin hydrochloride, a highly water-soluble drug, as a model drug, a sustainedrelease dosage form was developed. Six granule formulations were prepared from corn starchlactose, synthetic aluminum silicate, ethyl cellulose, and polymethylmethacrylate, and five tablet formulations were prepared from corn starch-lactose, calcium hydrogen phosphate, crystalline cellulose, ethyl cellulose, and sodium polyacrylate. These formulations were subjected to dissolution tests for in vitro screening of potential retard forms. It was found that incorporation of sodium polyacrylate was very effective in reducing the release rate. Two formulations incorporating sodium polyacrylate were selected as the most successful retard forms in an in vitro study. They were orally administered to beagle dogs for in vivo evaluation. It was concluded that this material is one of the most promising excipients for a sustained-release dosage form which contains an extremely water-soluble drug.View full abstractDownload PDF (693K) -
KEN MASUMOTO, KUMIKO MATSUMOTO, AKIYOSHI YOSHIDA, SHINICHI HAYASHI, NA ...1984 Volume 32 Issue 3 Pages 1055-1062
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate the pharmaceutical availability of the water-insoluble glucan produced by Streptococcus mutans, application of the glucan as a filler for sustained-release tablets was studied. Glucan alone or the combined powder of glucan with lactose was used as a filler for these tablets and chlorpheniramine maleate (CPM), a potent antihistaminic, was used as a medicament. When the concentration of glucan was higher than 60%, directly compressed tablets were very hard and scarcely disintegrated. The release of CPM from a single face of the tablets was linear when plotted as a function of the square root of time. The release rate of CPM increased with a decrease of the concentration of glucan. The amount of CPM released increased in proportion to the initial concentration of CPM when the amount of CPM in the tablet was less than 25mg. The effects of the tablet weight, the compressional pressure and the concentrations of glucan and CPM on the drug release rate from the whole tablets were also studied. Further, the release profile of the tablet containing glucan was compared with that of a commercial tablet containing the same active ingredient. In the case of the tablet containing glucan, in contrast to the commercial tablet, no gap was observed in the release profile when the dissolution medium was changed from No. 1 to No. 2 disintegration media in JPX. In conclusion, these results suggest that the water-insoluble glucan may be useful as a filler for directly compressed sustained-release tablets.View full abstractDownload PDF (846K) -
HIROSHI NAGAI, MINEO KIKUCHI, HIROYUKI NAGANO, MOTOHARU SHIBA1984 Volume 32 Issue 3 Pages 1063-1070
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe extent and mechanism of decomposition of Nicorandil [N-(2-hydroxyethyl) nicotinamide nitrate (ester)] (I) in aqueous solution at various pH values were clarified. Four products derived from (I) were isolated and identified as 2-(3-pyridyl)-2-oxazoline (II), 2-aminoethyl nicotinate nitrate (III), N-(2-hydroxyethyl) nicotinamide (IV) and nicotinic acid (V). The decomposition products and (I) were quantitated by high performance liquid chromatography. The decompositions of (I), (II) and (III) followed pseudo first-order kinetics, while (IV) and (V) did not decompose further in the range of pH 4 to 11. Arrhenius plots of the rate constant for (I) were linear and the apparent activation energy for (I) was 25kcal/mol at pH 7.0. The decomposition in aqueous solution was found to occur by a stepwise mechanism, with (I) cyclizing to form (II), which undergoes ring-opening to give (III), followed by competitive reactions, that is, rearrangement and hydrolysis, to form (IV) and (V) in the pH range of 4 to 11.View full abstractDownload PDF (700K) -
MAKOTO OTSUKA, NOBUYOSHI KANENIWA1984 Volume 32 Issue 3 Pages 1071-1079
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of grinding on the physicochemical properties of cephalexin (CEX) were studied by means of water content measurements, differential thermal analysis (DTA), differential scanning calorimetry (DSC), X-ray diffraction analysis and scanning electron microscopy (SEM). The water content of CEX which had been ground for 4h and converted to a noncrystalline state was proportional to relative humidity (RH) in the range of 0-62% RH, and was about 2 mol/mol at 62-82% RH. The water content of intact crystal phase IV was about 1 mol/mol at 20-75% RH, and about 2 mol/mol at 82-95% RH. The X-ray diffraction data indicated that ground CEX remains in the noncrystalline state until it has absorbed more than about 2 mol of water per mol. At 62% RH, the water content of phase IV increased with increasing grinding time due to the conversion to noncrystalline state. The dehydration point of the ground CEX was depressed by up to about 25°C with increasing grinding time, and the decomposition point of the ground products was depressed by up to about 30°C. In general, the physicochemical properties changed rapidly when the crystallinity of the ground product fell below about 25%. The activation energy and mechanism of dehydration were determined by using nonisothermal kinetic analysis (Criado's method). The dehydration of the product ground for 4h (noncrystalline solid) followed first-order kinetics and its activation energy and latent heat were calculated to be 14.83 kcal/mol and 8.31 kcal/mol, respectively. The product ground for 4h was about 2.5 times more soluble than intact phase IV. The dehydration behavior and solubility of the product ground for 4h were different from those of the freeze-dried product, even though both products are in a noncrystalline state.View full abstractDownload PDF (1415K) -
MASARU IKEDA, TSUNEJI NAGAI1984 Volume 32 Issue 3 Pages 1080-1090
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydrolysis reaction of oxazolam, a representative of 1, 4-benzodiazepinooxazoles (BDOZ), was investigated kinetically. The reaction product was identified by thin layer chromatography (TLC) and infrared (IR) spectroscopy, and it was concluded that irreversible hydrolytic cleavage took place at the diazepinone nucleus. The rate constant was determined by ultraviolet (UV) spectroscopy. The reaction was a first-order process consisting of two parallel reactions with different reacting species of oxazolam, depending on the pH of the medium. The pH-rate profile obtained for the reaction suggested that the reaction was independent of hydrogen ion concentration in acidic media, while it was catalyzed by hydroxide ion in alkaline media. The nonlinear least-squares fit method was employed to determine the catalytic rate constants involved in the equation describing the pH-rate constant relationship. Activation energies as well as other thermodynamic parameters were obtained in media of pH 2.0 and 8.0, and the values confirmed that different chemical species of oxazolam were involved. The observed effect of buffer concentration indicated that general base catalysis was involved in the reaction of the ionized species of oxazolam. A mechanistic consideration indicated that the rate-determining step may be the nucleophilic attack of a water molecule or hydroxide ion at the 11b-position in the diazepinone nucleus.View full abstractDownload PDF (938K) -
REIKO IWAOKU, YUHKO OKAMATSU, SHIGEMI KINO, KAZUHIKO ARIMORI, MASAHIRO ...1984 Volume 32 Issue 3 Pages 1091-1095
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhenobarbital was released fastest from Witepsol H15 suppository among four Witepsol bases tested. A coprecipitate of phenobarbital and povidone (ratio, 1 : 3) gave an X-ray diffraction pattern which indicates that the drug is in an amorphous form in the coprecipitate, and the dissolution and permeation patterns of the drug from the coprecipitate indicated that drug dissolution from the coprecipitate was rapid. Release of the drug from a Witepsol H15 suppository containing the coprecipitate was faster than that from Witepsol H15 containing the drug alone or containing a physical mixture of the two components. Administration of the suppository containing the coprecipitate also gave the highest blood levels of the drug.View full abstractDownload PDF (539K) -
EIJI MIZUTA1984 Volume 32 Issue 3 Pages 1096-1105
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new in vitro model has been elaborated for the simulation of plasma concentration curves based on the two-compartment open model. The new method consists of a procedure in which vessels containing water or an aqueous solution of a drug are simply connected in a line and the contents are made to flow at a constant rate from one side to the other. The model is expected to be useful for the study of, for example, the in vitro antibacterial activity of antibiotics whose concentrations change according to the two-compartment open model.View full abstractDownload PDF (857K) -
YUKIO MORI, FUSAYUKI YOKOYA, YOSHIYUKI SAKAI, KAZUMI TOYOSHI, SHIGEO B ...1984 Volume 32 Issue 3 Pages 1106-1112
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe disposition and metabolism of DL-2-(4-(2-thienylcarbonyl) phenyl) propionic acid (suprofen, S) were evaluated in male and female mice. The radiometric findings following oral administration of 2mg/kg of 3H-S to male and female mice showed similar patterns of absorption, distribution, and excretion of the radioactivity. S was rapidly absorbed in mice of both sexes ; blood levels after a single oral dose of 2 mg/kg of 3H-S reached maxima within 7.5 min. Blood radioactivity was mostly accounted for by unchanged S. Elimination of 3H-S from the blood was rapid ; most of the radioactivity was excreted in the urine and a portion in the feces within 24h after oral administration of 2mg/kg of 3H-S or 10mg/kg of 14C-S. The only tissues with concentrations similar to or higher than that in the plasma were those involved in metabolism and excretion (liver and kidney) ; other tissue levels, except for the stomach, were all very low and there was no evidence of accumulation of drug-related material in any tissue. Male mouse urine contained S, 2-(4-(2-thienylhydroxymethyl) phenyl) propionic acid, 2-(4-carboxyphenyl) propionic acid, and two unknown metabolites, accounting for about 73% of the urinary radioactivity.View full abstractDownload PDF (742K) -
JENNIFER J. BOEHM, ROLLAND I. POUST1984 Volume 32 Issue 3 Pages 1113-1119
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influences of temperature, pH, buffer, ionic strength and initial drug concentration on the stability of succinylcholine chloride in aqueous solution were investigated. The following results were obtained : (i) in unbuffered solutions-the reaction was apparent zero order ; the pH fell during the course of reaction ; the rate of hydrolysis was slowest in solutions initially adjusted to pH 3.75-4.50, (ii) the rate of hydrolysis was significantly catalyzed by buffer, (iii) the rate of hydrolysis increased modestly with an increase in ionic strength, and (iv) the rate of hydrolysis increased with initial concentration of drug in solution.View full abstractDownload PDF (657K) -
MASANORI TAKAOKA, HIROKO AKIYAMA, HIROFUMI OKAMURA, SHIRO MORIMOTO1984 Volume 32 Issue 3 Pages 1120-1125
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSExcretion patterns of urinary enzymes having amidolytic and esterolytic activities were examined in the urine of male and female rats. Kallikrein and non-kallikrein [esterase A1 (EA1) and esterase A2 (EA2)] fractions were separated by diethylaminoethyl-cellulose chromatography and amidolytic and esterolytic activities were assayed by using prolyl-phenylalanyl-arginine-4-methylcoumaryl-7-amide and N-α-tosyl-L-arginine methyl ester. In male rat urine, about 25% of total esterolytic activity was due to kallikrein, and the remainder was attributable to EA1 and EA2. In female rat urine, about 45% of total esterolytic activity was due to kallikrein and the remainder was mostly attributable to EA2. EA1 in female rats accounted for less than one-tenth of total esterolytic activity. On the other hand, about 87 and 13% of total amidolytic activity were due to kallikrein and EA2, respectively, in both male and female rats. However, EA1 had no amidolytic activity. These findings indicate that most of the urinary amidolytic activity in both sexes is associated with kallikrein, in contrast to urinary esterolytic activity, and that EA1 is not relevant to the results of urinary amidolytic assay.View full abstractDownload PDF (665K) -
SABURO SUGAI, YOSHIHIRO HASEGAWA, YOSHIO KAJIWARA, SEIICHIRO YOSHIDA, ...1984 Volume 32 Issue 3 Pages 1126-1134
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwenty-one derivatives of 4-acyloxy-1-(1, 3-dioxolan-2-ylmethyl) piperidines (2) and their quaternary salts (6) were synthesized and tested for anticholinergic activities. The piperidine derivatives (2) exhibit moderate activities. Among the quaternary salts (6), the trans-isomers were always more active than the corresponding cis-isomers.View full abstractDownload PDF (881K) -
SEIICHI INAYAMA, KENZO HARIMAYA, HITOSHI HORI, TAMIKO OHKURA, TAKESHI ...1984 Volume 32 Issue 3 Pages 1135-1141
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA less lipophilic non-sesquiterpenoid antitumor constituent, methyl caffeate, along with D-fructose, was isolated from the aqueous methanol extract of the dried whole plant of Gaillardia pulchella. Among forty-three synthetic catechol analogues related to methyl caffeate tested for antitumor activity against Sarcoma 180 in mice, acetates of methyl catecholylpropionoid type showed stronger activity than the corresponding catechuic acid and catechualdehyde derivatives as well as simple benzaldehyde (so-called vidrol). None of the catecholic and related compounds tested showed significant antimicrobial activity in vitro.View full abstractDownload PDF (727K) -
NAOHITO OHNO, IWAO SUZUKI, SHOZO OIKAWA, KICHIRO SATO, TOSHIO MIYAZAKI ...1984 Volume 32 Issue 3 Pages 1142-1151
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPolysaccharides in the cultured fruit body of Grifola frondosa were extracted successively with hot water, aqueous zinc chloride, and cold and hot aqueous sodium hydroxide containing urea. The antitumor effect and structural features of the extracted compounds were examined. The above extraction gave water-soluble glucan fractions together with water-insoluble heteroglycan fractions. The heteroglycan fractions were composed of glucose, xylose and mannose. The zinc chloride extraction gave only a small quantity of polysaccharide. The structural characteristics of these polysaccharides were deduced from the results of gel filtration, methylation, enzymic degradation, and 13C-nuclear magnetic resonance (NMR) spectroscopy. The hot water extract contained a large amount of α-1, 4-glycosidic linkages (about 50%) digestable by α-amylase, and also contained α-1, 6-, β-1, 6-, and β-1, 3-linkages. The water-soluble glucan fractions extracted with cold and hot sodium hydroxide contained more 6-branched glucosyl unit in every three 3-substituted β-glucosyl units. All of these water-soluble and insoluble fractions showed potent antitumor activity against the solid form of Sarcoma 180 tumor in ICR mice. The activity of the hot sodium hydroxide extractable, water-soluble fraction was the strongest. The antitumor activity was positively correlated with the content of 6-branched β-1, 3-glucan in these water-soluble fractions.View full abstractDownload PDF (886K) -
SHIGEHIRO MORICHI, EIJI SAKO, EIICHI HASEGAWA, TADAKAZU SUYAMA, HIROSH ...1984 Volume 32 Issue 3 Pages 1152-1162
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSKallikrein was highly purified from 1000 liters of fresh pooled urine collected from healthy men by the following procedure : silica gel adsorption, gel filtration on Sephadex G-75, DEAE-Sephadex chromatography, bentonite treatment, affinity chromatography on aprotinin-Sepharose 4B, and rapid gel filtration on a TSK Gel G-3000 SWG column. The final preparation, 17mg of human urinary kallikrein (HUK), was purified 621.6-fold from the crude preparation obtained by silica gel adsorption. One mg of HUK showed activities of 5.58 PNA units toward H-D-Val-Leu-Arg-pNA, and about 1100 kallikrein units in the dog hypotensive assay. HUK thus isolated was found to be pure by means of disc electrophoresis, immunoelectrophoresis, and gel filtration. The following enzymes and bioactive substances were not detected : kininase, urokinase, caseinolytic proteases, blood group substances, substances affecting plasma coagulation, and pyrogens. On isoelectric focusing, HUK separated into microheterogeneous components. The pI's of the dominant components were 3.5, 3.8, and 4.1, while the corresponding molecular weights were 5.4×104, 4.9×104, and 4.4×104, respectively. An aqueous solution of HUK was stable in the pH range from 6 to 12, and was also stable at 60°C for 2h at neutral pH. Michaelis constants were from 4.0×10-5 to 4.0×10-4M toward five kinds of synthetic substrates conventionally used for HUK assay. Optimal pH's for these substrates and human kininogen were in the alkaline pH range of 7.5 to 11.5.View full abstractDownload PDF (1149K) -
NORIO KAWAHARA, TAKAKO NAKAJIMA, TSUNEO ITOH, HIROAKI TAKAYANAGI, HARU ...1984 Volume 32 Issue 3 Pages 1163-1169
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBenzoxazole and o-aminophenol each reacted with dimethyl acetylenedicarboxylate (DMAD) to give the same product, which was previously suggested to be a [1, 4] benzoxazine [2, 3-b] pyran derivative (2). An X-ray crystallographic analysis has now shown the structure of this compound to be trimethyl 2, 3-dihydro-2-oxo-4H-1, 4-benzoxazine-△3.7-aconitate. A similar treatment of o-aminophenols and β-aminoalcohols with an excess of DMAD afforded new 1, 4-benzoxazines and 1, 4-oxazines, respectively.View full abstractDownload PDF (689K) -
MASANORI SAKAMOTO, TAKASHI AKIMOTO, YASUNOBU AKIYAMA, KYOKO FUKUTOMI, ...1984 Volume 32 Issue 3 Pages 1170-1173
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of 1-alkyl-3, 4-dihydroisoquinolines (4a-d) with 4-nitrobenzoyl cyanide (2) gave the indolizine derivatives 5a-c and 6d, respectively. Compounds 4a and 4b also reacted with diketene (8) to give the quinolizinone derivatives 9a, b, respectively.View full abstractDownload PDF (519K) -
ATSUSHI NUMATA, MICHIKO NABAE, EIICHI UEMURA1984 Volume 32 Issue 3 Pages 1174-1177
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was observed that in numerous phenols the phenolic hydroxyl and ortho proton resonances in the proton nuclear magnetic resonance (1H NMR) spectrum moved downfield on addition of anhydrous magnesium chloride to the dimethyl sulfoxide-d6 or dimethylformaide-d7 solution. The selective shifts of phenolic ortho proton resonances in the presence of magnesium chloride were shown to be a useful tool for 1H NMR signal assignments and structure elucidation of naturally occurring phenols.View full abstractDownload PDF (445K) -
JUNKO MARUYAMA, KEIICHI ITO1984 Volume 32 Issue 3 Pages 1178-1182
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPreparations of the ring-fused 4-methylcoumarins 2-10 were reexamined, and the nuclear magnetic resonance (NMR), ultraviolet (UV) and fluorescence spectral characteristics were determined. Fluorescence properties were found to be sensitive to the type and the position of the ring fused to the parent 4-methylcoumarin 1. The angularly benzo-fused 3 was highly fluorescent, whereas the linearly benzo-fused 4 and the pyrono-fused 7 and 9 were only weakly fluorescent.View full abstractDownload PDF (524K) -
NAOKI MITSUO, HIROSHI TAKEICHI, TOSHIO SATOH1984 Volume 32 Issue 3 Pages 1183-1187
Published: March 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLactase from Kluyveromyces lactis was found to have high transglucosylation activity, transferring the glucosyl group of aryl glucoside to an alcoholic hydroxyl group in high yield. Both primary and secondary alcohols can accept the glucosyl group. Transglucosylation to glycol yielded a single kind of glucoside. A very hydrophilic alcohol, such as glycerol, could not serve as a substrate in this system. Hydrophobic alcohols slightly soluble in water were glucosylated in a two-phase system consisting of water and an organic solvent immiscible with water.View full abstractDownload PDF (532K)