Solution syntheses of two enkephalin-containing peptides, peptide E and dynorphin(1-24), using Nin-(2,4,6-triisopropylphenylsulfonyl)tryptophan.


:Two enkephalin-containing peptides, peptide E and dynorphin(1-24), were synthesized by conventional solution methods employing a new Trp derivative, Nin-(2,4,6-triisopropylphenylsulfonyl)tryptophan [Trp(Tps)]. All protecting groups employed including the Tps group were removed by treatment with 1 M trifluoromethanesulfonic acid (TFMSA)-thioanisole in trifluoroacetic acid (TFA) at the final steps of these syntheses. Subsequent purifications by Sephadex G-25 chromatography, CM-Biogel A ion exchange chromatography, and reversed-phase high-performance liquid chromatography afforded highly purified samples. Both synthetic peptide E and dynorphin(1-24) exhibited high in vitro opioid activity. The usefulness of this new tryptophan derivative for practical peptide synthesis was established through these syntheses of complex Trp-containing peptides.


Kitagawa K,Kawamoto T,Futaki S,Kiyama S,Akita T,Moritoki H,Kiso Y




Has Abstract


1989-10-01 00:00:00












  • Statistical Analysis of the Impact of Molecular Descriptors on Cytotoxicity of Thiourea Derivatives Incorporating 2-Aminothiazole Scaffold.

    abstract::Chemical reactivity descriptors and lipophilicyty (log P) were evaluated via semi-empirical method for the quantum calculation of molecular electronic structure (PM3) in order to clarify the structure-cytotoxic activity relationships of disubstutited thioureas. Analysed compounds were obtained by the linkage of 2-amin...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Filipowska A,Filipowski W,Tkacz E,Nowicka G,Struga M

    更新日期:2016-01-01 00:00:00

  • Cross-link dimer formation of the acetaldehyde-derived cyclic 1,N(2)-Propano-2'-deoxyguanosine adduct using electrochemical oxidation.

    abstract::The electrochemically oxidative lesion of the acetaldehyde-derived cyclic propano adduct 2 of 2'-deoxyguanosine 1 was identified as the cross-linked dimer 4 of adduct 2. Cross-link formation is explained by the nucleophilic preference of the exocyclic amino group in 2 to the carbocation 3 electrogenerated by 1-proton ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Murakami H,Esaka Y,Uno B

    更新日期:2009-12-01 00:00:00

  • Change of ras-transformed NRK-cells back to normal morphology by mycalamides A and B, antitumor agents from a marine sponge.

    abstract::Mycalamide A and mycalamide B, isolated as antiviral and antitumor agents from a New Zealand sponge of the genus Mycale, converted the morphology of ras-transformed NRK-cells to normal morphology at 10 and 1 ng/ml, respectively. The effect on protein synthesis suggests that these agents converted the morphology by pre...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Ogawara H,Higashi K,Uchino K,Perry NB

    更新日期:1991-08-01 00:00:00

  • Oleanene-type triterpene glycosides from puerariae radix. IV. Six new saponins from Pueraria lobata.

    abstract::From Puerariae Radix, the root of Pueraria lobata (Leguminosae), six new oleanene-type triterpene glycosides, called kudzusaponins A1 (1), A2 (2), Ar (3), SA4 (5), and SB1 (6) were isolated together with kudzusaponin A3 (7), soyasaponins SA3 (8), and I (9). The structures of 1-6 were determined to be 3-O-alpha-L-rhamn...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Arao T,Kinjo J,Nohara T,Isobe R

    更新日期:1997-02-01 00:00:00

  • Spectroscopic analysis of charge transfer complex formation between neuroleptics and iodine.

    abstract::Molecular interactions between iodine and various neuroleptics were investigated by UV/Vis spectroscopy. Iodine was found to form charge transfer complexes in a 1:1 stoichiometry and of n-sigma type with these molecules. The values of the formation constants Kc of these iodinated complexes indicate a strong donor-acce...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Comby F,Jambut-Absil AC,Buxeraud J,Raby C

    更新日期:1989-01-01 00:00:00

  • Phenylpropanoids from Umbilicus pendulinus.

    abstract::Phytochemical investigation of the leaves of Umbilicus pendulinus afforded in addition to 2-O-caffeoyl malate, isoquercitrin and Z-venusol, the new isomer E-venusol. Special NMR experiments were carried out to elucidate the configuration of the two latter compounds. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Viornery L,Saliba C,Daskiewicz JB,Bayet C,Comte G,Fenet B,Gutierrez G,Barron D

    更新日期:2000-11-01 00:00:00

  • Application of Terahertz Attenuated Total Reflection Spectroscopy to Detect Changes in the Physical Properties of Lactose during the Lubrication Process Required for Drug Formulation.

    abstract::Manufacturing the solid dosage form of an orally administered drug requires lubrication to enhance manufacturability, ensuring that critical quality attributes such as disintegration and dissolution of the drug product are maintained during manufacture. Here, to evaluate lubrication performance during manufacture, we ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Dohi M,Momose W,Yamashita K,Hakomori T,Sato S,Noguchi S,Terada K

    更新日期:2017-02-01 00:00:00

  • Transport of harman alkaloids across Caco-2 cell monolayers.

    abstract::This study examined the intestinal transport of five harman alkaloids using the Caco-2 cell monolayer as a model of the human intestinal mucosa. Transport parameters, permeability coefficients and percent transports, were calculated and compared under identical conditions with atenolol. Permeability coefficients were ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Khan SI,Abourashed EA,Khan IA,Walker LA

    更新日期:2004-04-01 00:00:00

  • Facile synthesis and quantitative structure-activity relationship study of antitumor active 2-(4-oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles.

    abstract::2-(5-Arylidene-4-oxo-3-phenyl-thiazolidin-2-ylidene)-3-oxo-propionitriles 4a-j were prepared via condensation of aromatic aldehydes with 4-thiazolidinones 3a,b. The latter was obtained via electrophilic attack of phenylisothiocyanate on 3-oxo-propionitriles 1a,b followed by reaction with chloroacetyl chloride under ba...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Hanna MM,George RF

    更新日期:2012-01-01 00:00:00

  • Synthesis and antibacterial activities of optically active substituted 1,2-dihydro-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids.

    abstract::A series of optically active substituted 1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids was prepared via optically active 2-methyl-4,5-difluoroindoline (10) and tested for antibacterial activities. Among them, (2S)-9-[(3R,1'S)-3-(1'-amino)ethyl-1-pyrrolidinyl]-8-fluoro-1,2-dihydro- 2- methyl-6-oxo-6H-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Tsuji K,Tsubouchi H,Ishikawa H

    更新日期:1995-10-01 00:00:00

  • Tannins and related polyphenols of euphorbiaceous plants. XI. Three new hydrolyzable tannins and a polyphenol glucoside from Euphorbia humifusa.

    abstract::Three new hydrolyzable tannins, euphormisins M1, M2, and M3, were isolated from Euphorbia humifusa WILLD., and respectively characterized as 1,3,6-tri-O-galloyl-4-O- brevifolincarboxyl-beta-D-glucose (19), an oxidative metabolite (23) of geraniin, and 1,3,6-tri-O-galloyl-alpha-D-glucose (18), by spectroscopic and chem...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Yoshida T,Amakura Y,Liu YZ,Okuda T

    更新日期:1994-09-01 00:00:00

  • Oxidative Stress Is Involved in the Renal Dysfunction Induced by Sinoaortic Denervation in Rats.

    abstract::The hypothesis that oxidative stress contributes to renal dysfunction in sinoaortically denervated (SAD) rats was investigated. Rats were sinoaortically denervated and received treatment with tempol (0.5 mmol/L in drinking water) for 8 weeks. Although the tempol treatment of the SAD rats had no significant effect on b...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Sun Y,Fan J,Chai D,Zhang M

    更新日期:2016-10-01 00:00:00

  • Preparation of 4-pentenoic acid ester of Neu5Ac and 4-pentenyl glycoside of Neu5Ac and their application to glycosylation.

    abstract::Novel sialosyl donors, 4-pentenoic acid ester of N-acetylneuraminic acids (Neu5Ac) and 4-pentenyl glycoside of Neu5Ac were successfully prepared from the corresponding per-O-acetylated 2-hydroxy and 2-chloro derivatives of Neu5Ac, respectively and applied to the synthesis of O-sialosides. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Ikeda K,Fukuyo J,Sato K,Sato M

    更新日期:2005-11-01 00:00:00

  • Heptacoordinate tin(IV) compounds derived from pyridine Schiff bases: synthesis, characterization, in vitro cytotoxicity, anti-inflammatory and antioxidant activity.

    abstract::Tin(IV) complexes 2a--q derived from pyridine Schiff bases were prepared and characterized. Four complexes of this series were evaluated in vitro against different carcinogenic cell lines; besides their anti-inflammatory and antioxidant properties were also tested. Combination of mass spectrometry, multinuclear NMR an...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: González A,Gómez E,Cortés-Lozada A,Hernández S,Ramírez-Apan T,Nieto-Camacho A

    更新日期:2009-01-01 00:00:00

  • New abietane-type diterpenes from the heartwood of Picea morrisonicola.

    abstract::New abietane-type diterpenes, 15-acetoxy-7-oxodehydroabietic acid (1), picealactones A (2), B (3), and C (4), together with the known 7-oxodehydroabietic acid (5) were isolated and identified from the heartwood of Picea morrisonicola. The structures of 1-4 were determined on the basis of spectral data explanation. Com...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Kuo YH,Yeh MH,Lin HC

    更新日期:2004-07-01 00:00:00

  • The reaction of (4R,5R)- and (4S,5S)-4,5-epoxy-2(E)-hexenoates and secondary amines.

    abstract::A reaction of methyl (4R,5R)-4,5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R,5R)-4,5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S,5R)-4-N-benzyl-methylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (-)-osmundalactone 11, which...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Saotome C,Ono M,Akita H

    更新日期:2001-07-01 00:00:00

  • New friedelane triterpenoids with antimicrobial activity from the stems of Drypetes paxii.

    abstract::Two new friedelane-type triterpenes named 12alpha-hydroxyfriedelane-3,15-dione and 3beta-hydroxyfriedelan-25-al, together with six known compounds were isolated from the stems of Drypetes paxii Hutch. (Euphorbiaceae). Their structures were established on the basis of conventional 1 dimensional (1D) NMR methods, 2D shi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Chiozem DD,Trinh-Van-Dufat H,Wansi JD,Mbazoa Djama C,Fannang VS,Seguin E,Tillequin F,Wandji J

    更新日期:2009-10-01 00:00:00

  • Characterization of sodium hypochlorite degradation of beta-glucan in relation to its metabolism in vivo.

    abstract::Soluble (SSG, beta-1,3-D-glucan obtained from the culture filtrates of a fungus, Sclerotinia sclerotiorum IFO 9395) and particulate (zymosan) beta-glucans were oxidized by sodium hypochlorite (NaClO), and the oxidized products were analyzed by gel filtration and ion-exchange chromatographies and by limulus G-test to s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Miura NN,Ohno N,Adachi Y,Yadomae T

    更新日期:1996-11-01 00:00:00

  • Presence of the basement membrane component--heparan sulfate proteoglycan--in bovine lens capsules.

    abstract::Heparan sulfate proteoglycan was extracted from bovine lens capsules by 0.45 M NaCl/2 M urea and purified using ion-exchange chromatography and gel filtration. The proteoglycan was found to consist of protein and carbohydrate in a ratio of 75 to 25. The estimated average molecular weight of the heparan sulfate proteog...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Onodera S

    更新日期:1991-04-01 00:00:00

  • Total Synthesis and Anticancer Activity of Novel Pulsatilla Saponin D Analogues.

    abstract::Novel saponins that retain a free carboxyl group at the C-17 position and various sugars linked at the C-3 position of hederagenin aglycone were synthesized via stereospecific glycosylation. Since these natural products represented by Pulsatilla saponin D (PSD) were obtained in very small amounts, the total synthesis ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Kim M,Park Y,Chung WY,Park KK,Jung M

    更新日期:2015-01-01 00:00:00

  • New cyclopropyl-triterpenoids from the aerial roots of Ficus microcarpa.

    abstract::Four new cyclopropyl-triterpenes, 27-nor-3beta-hydroxy-25-oxocycloartane (1), (22E)-25,26,27-trinor-3beta-hydroxycycloart-22-en-24-al (2), 3beta-acetoxy-15alpha-hydroxy-13,27-cyclours-11-ene (3), 3beta-acetoxy-12alpha-formyloxy-13,27-cycloursan-11alpha-ol (4), together with (23E)-27-nor-3beta-hydroxycycloart-23-en-25-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Chiang YM,Su JK,Liu YH,Kuo YH

    更新日期:2001-05-01 00:00:00

  • Efficient synthesis of a key intermediate of DV-7751 via optical resolution or microbial reduction.

    abstract::Two efficient and practical methods of synthesis of the C-10 substituent of DV-7751 (1), a novel quinolone carboxylic acid, were established. The first method utilizes an optical resolution of racemic 8-amino-6-benzyl-6-azaspiro[3.4]octane (13), while the second employs an enantioselective microbial reduction of 6-ben...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Miyadera A,Satoh K,Imura A

    更新日期:2000-04-01 00:00:00

  • Amino acid derivatives with anticonvulsant activity.

    abstract::A series of benzylamides of N-alkylated, N-acylated or free nine cyclic and one linear amino acids as potential anticonvulsants have been synthesized. The structures of the obtained compounds were designed on the basis of the previously determined structure and physicochemical properties/anticvonvulsant activity relat...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Paruszewski R,Strupińska M,Stables JP,Swiader M,Czuczwar S,Kleinrok Z,Turski W

    更新日期:2001-05-01 00:00:00

  • Synthesis, characterization, cytotoxic activities, and DNA-binding studies of ternary copper(II) complexes with new coumarin derivatives.

    abstract::In this study, two novel complexes [Cu(MCVH)phen(H(2)O)].ClO(4) (1) and [Cu(MCLH)phen(H(2)O)].ClO(4) (2) (here, MCVH(2)=(7-hydroxy-4-methyl-8-coumarinyl) valine, MCLH(2)=(7-hydroxy-4-methyl-8-coumarinyl) leucine) have been synthesized and characterized by elemental analyses, molar conductance, infrared spectra (IR), (...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Jia L,Xu XM,Xu J,Chen LH,Jiang P,Cheng FX,Lu GN,Wang Q,Wu JC,Tang N

    更新日期:2010-08-01 00:00:00

  • Studies on cognitive enhancing agents. I. Antiamnestic and antihypoxic activities of 2-dimethylaminoethyl ethers and related compounds.

    abstract::N-(2-Dimethylaminoethyl)carboxamide (1a-d), 2-dimethylaminoethyl alkyl ether (2a, b), and 2-dimethylaminoethyl 2-hydroxy-2-phenethyl ether (3a-c) and its amino and methylene analogues (3d, 4) have been screened for antiamnestic and antihypoxic activities in mice. A clear reversing effect on electroconvulsive shock-ind...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Ono S,Yamafuji T,Chaki H,Todo Y,Maekawa M,Kitamura K,Tai M,Narita H

    更新日期:1995-09-01 00:00:00

  • Preparation of N'-[2-(5,6-dimethylbenzothiazolyl)]-N-furfuryloxamide with plant growth regulatory activity.

    abstract::The reaction of the N-furfuryloxamic acid sodium salt (12) with 1,1'-oxalyldiimidazole (ODI) yielded the imidazolide (13) as an intermediate, and this directly reacted with 2-aminothiazole derivatives (14) or 2-aminobenzothiazole derivatives (15) under essentially neutral conditions to afford the N'-12-(substituted th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Kitagawa T,Tsutsui C

    更新日期:2000-09-01 00:00:00

  • Lobophytones H-N, Biscembranoids from the Chinese soft coral Lobophytum pauciflorum.

    abstract::Chemical examination of a Chinese soft coral Lobophytum pauciflorum resulted in the isolation of seven new biscembranoids, named lobophytones H-N (1-7). Their structures were determined by interpretation of 1D- and 2D-NMR (correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear mu...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Yan P,Deng Z,van Ofwegen L,Proksch P,Lin W

    更新日期:2010-12-01 00:00:00

  • Junceols D-H, new polyoxygenated briaranes from sea whip gorgonian coral Junceella juncea (Ellisellidae).

    abstract::Chemical investigations on the sea whip gorgonian coral Junceella juncea have led to the isolation of five new 8-hydroxybriarane diterpenoids, junceols D-H (1-5). The structures of briaranes 1-5 were determined on the basis of spectroscopic methods and the methylenecyclohexane rings were found to exist in boat form in...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Sung PJ,Pai CH,Hwang TL,Fan TY,Su JH,Chen JJ,Fang LS,Wang WH,Sheu JH

    更新日期:2008-09-01 00:00:00

  • Novel 4-phenoxy-2-(1-piperazinyl)quinazolines as potent anticonvulsive and antihypoxic agents.

    abstract::A series of 4-phenoxy-2-(1-piperazinyl)quinazolines was synthesized and examined for anticonvulsive and antihypoxic activities. Many of the compounds exhibited potent anticonvulsive activity comparable to that of carbamazepine or phenytoin. Among them, 4-phenoxy-2-(4-propyl-1-piperazinyl)quinazoline (5w) was selected ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Hori M,Iemura R,Hara H,Ozaki A,Sukamoto T,Ohtaka H

    更新日期:1990-03-01 00:00:00

  • Studies on the constituents of Gardenia species. III. New iridoid glycosides from the leaves of Gardenia jasminoides cv. fortuneana Hara.

    abstract::Two new iridoid glycosides, 7 beta,8 beta-epoxy-8 alpha-dihydrogeniposide (1) and 8-epiapodantheroside (2), were isolated, together with six known (3-8) and three artifact (9-11) iridoids, from the leaves of Gardenia jasminoides cv. fortuneana Hara. Their structures were established based on chemical and spectral data...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章


    authors: Machida K,Takehara E,Kobayashi H,Kikuchi M

    更新日期:2003-12-01 00:00:00