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  • 1.
    Antoni G., Amschler H., Zech K., Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Synthesis of [18F]labelled roflumilast using difluoro[18F]bromo methane as alkylating agent2001In: Synthesis and Applications of Isotopically LabelledArticle in journal (Refereed)
  • 2.
    Antoni G., Ögren M., Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Enzymes as catalysts in labelling synthesis using short-lived radionuclides2001In: Synthesis and Applications of Isotopically LabelledArticle in journal (Refereed)
  • 3.
    Arvidsson P., Frackenpohl J., Ryder N., Liechty B., Petersen F., Zimmermann H., Camenisch G., Woessner R., Seebach D.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    On the antimicrobial and hemolytic activities of amphiphilic B-peptides.2001In: ChemBioChem, no 2(10), p. 771-773Article in journal (Refereed)
  • 4.
    Arvidsson P., Ruepling M., Seebach D.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Design, machine synthesis, and NMR-solution structure of a B-heptapeptide forming a saltbridge stabilized 314-helix in methanol and in water2001In: Chemical Communications (Cambridge, U K), p. 649-650Article in journal (Refereed)
  • 5.
    Bergson, G., Matsson, O.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Daniel Strömholm, The Svedberg och isotoperna2001In: Acta Academica Regiae Scientiarum Upsaliensis, ISSN ISBN 91-85832-14-6, Vol. 21, p. 53-60Article in journal (Other scientific)
  • 6.
    Bollmark, Martin
    Stockholm University.
    Studies on the synthesis of nucleotide analogues containing P-F and P-Se bonds2001Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In the present work, new synthetic approaches to the synthesis of nucleoside phosphorofluoridate and phosphorofluoridothioate diesters have been developed. These procedures involve either oxidative transformation of the corresponding H-phosphonate or H-phosphonothioate diesters in the presence of fluoride anion or iodine-promoted desulfurization of phosphorothioate or phosphorodithioate diesters in the presence of fluoride anion. Also, efficient protocols for the synthesis of nucleoside phosphorofluoridate, nucleoside phosphorofluoridothioate and nucleoside phosphorofluoridodithioate monoesters were developed.

    Furthermore, the chemistry of a new class of P(III) compounds containing selenium, i. e. H-phosphonoselenoate monoesters was developed and synthetic procedures for the conversion of these compounds into the corresponding diesters were designed. In addition, the usefulness of H-phosphonoselenoate diesters for the preparation of various selenium-containing nucleotide analogues was demonstrated.

    Finally, the possibility of employing triphenylphosphine selenide as a reagent for selenizing P(III) compounds was examined. Under mild conditions, this commercially available reagent was found to convert phosphite triesters and H-phosphonate diesters efficiently into the corresponding phosphoroselenoate derivatives.

  • 7.
    Bonasera T., Grue-Sorensen G., Ortu G., Binderup E., Bergström M., Björkling F., Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    The Synthesis of [26,27-11C]dihydroxyvitam in D3, a tracer for positron emission tomography (PET)2001In: Bioorganic & Medical Chemistry, no 9(12), p. 3123-312Article in journal (Refereed)
  • 8.
    Enblad P., Frykholm P., Valtysson J., Silander H C., Andersson J., Fasth K J., Watanabe Y., Långström B., Hillered L., Persson L.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Middle cerebral artery occlusion and reperfusion in primates monitored by microdialysis and sequential positron emission tomography2001In: Stroke, no 32 (7), p. 1574-80Article in journal (Refereed)
  • 9.
    Engman L., Kanada T., Gallegos A., Williams R., Powis G.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Water-soluble organotellurium compounds inhibit thioredoxin reductase and the growth of human cancer cells2001In: Anti-Cancer Drug Design, Vol. 2000, no 1, p. 330-Article in journal (Refereed)
  • 10.
    Frackenpohl J., Arvidsson P., Schreiber J., Seebach D.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    The outstanding biological stability of B- and Y-peptides toward proteolytic enzymes: an in vitro nvestigation with fifteen peptidases2001In: ChemBioChem, no 2(6), p. 445-455Article in journal (Refereed)
  • 11.
    Frykholm P., Hillered L., Långström B., Watanabe Y., Bergström M.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Increase of interstitial glycerol reflects the degree of ischaemic brain damage: a PET and microdialysis study in a middle cerebral artery occlusionreperfusion primate model2001In: Journal of Neurology, Neurosurgery And Psychiatry, no 2, p. 455-61Article in journal (Refereed)
  • 12.
    Gaul C., Arvidsson P., Bauer W., Gawley R., Seebach D.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Computational reactIR-, and NMR-spectroscopic investigations on the chiral formyl anion equivalent N-(a-lithiomethylthiomet hyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one and related compounds2001In: Chemistry--A European Journal, no 7 (19), p. 4117-4125Article in journal (Refereed)
  • 13. Gordon, C M
    et al.
    Ohlin, C A
    Ritchie, C
    Ionic liquids: Clean solvents for organic synthesis.2001Other (Refereed)
  • 14.
    Johansson, Tommy
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kers, Annika
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    2-Pyridylphosphonates: A New type of Modification for Nucleotide Analogues2001In: Tetrahedron Letters, ISSN 0040-4039, Vol. 42, no 11, p. 2217-2220Article in journal (Refereed)
    Abstract [en]

    Suitably protected dithymidine H-phosphonates afforded the corresponding dinucleoside 2-pyridylphosphonates upon treatment with N-methoxypyridinium tosylate in acetonitrile in the presence of 1,8-diazabicylo[5.4.0]undec-7-ene (DBU). The reaction was rapid (ca. 5 min), practically quantitative and proceeded stereospecifically, most likely with retention of configuration at the phosphorus centre.

    A simple and efficient protocol for the preparation of a new type of oligonucleotide analogue bearing a 2-pyridylphosphonate internucleotide linkage was developed

  • 15.
    Johansson, Tommy
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Dinucleoside Pyridylphosphonates Involving Palladium(0)-catalysed Phosphorus-carbon Bond Formation as a Key Step2001In: Chemical Communications, ISSN 1359-7345, no 24, p. 2564-2565Article in journal (Refereed)
    Abstract [en]

    Dinucleoside 3-pyridylphosphonates, as well as their 2- and 4-pyridyl positional isomers, have been synthesised using a palladium(0)-catalysed cross coupling strategy

  • 16.
    Johansson, Tommy
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    The Case for Configurational Stability of H-Phosphonate Diesters in the Presence of Diazabicyclo[5.4.0]undec-7-ene (DBU)2001In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, Vol. 9, no 9, p. 2315-2322Article in journal (Refereed)
    Abstract [en]

    Configurational stability of dinucleoside H-phosphonates and the stereochemical course of their sulfurisation in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU) were investigated using 31P NMR spectroscopy. It was found that under the reaction conditions and irrespective of the type of protecting groups present in the nucleoside moieties, the H-phosphonate diesters investigated did not undergo any detectable epimerisation at the phosphorus centre, and their sulfurisation with elemental sulfur in the presence of DBU, proceeded stereospecifically. Thus, we could not confirm reports from another laboratory on a stereoselective course of sulfurisation of H-phosphonate diesters and the corresponding acylphosphonates in the presence of DBU.

  • 17.
    Karimi F., Kihlberg T., Långström B
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    [11C]/(13C)Carbon monoxide in palladium-mediated synthesis of imides2001In: Journal of the Chemical Society, Perkin Transactions 2, p. 1528-1531Article in journal (Refereed)
  • 18.
    Kihlberg T., Antoni G., Björkman M., Karimi F., Rahman O., Ögren M., Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    [11C]Carbon monoxide has become a versatile precursor2001In: Synthesis and Applications of Isotopically LabbelledArticle in journal (Refereed)
  • 19.
    Kritikos, M
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Moustiakimov, M
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Wijk, M
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Westin, Gunnar
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Materials Chemistry, Inorganic Chemistry. oorganisk kemi.
    Synthesis, structure and characterisation of Ln(5)O(OPri)(13) with Ln = Nd, Gd or Er2001In: JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, ISSN 1472-7773, no 13, p. 1931-1938Article in journal (Refereed)
    Abstract [en]

    The molecular and basically isostructural oxo-alkoxides Ln(5)O(OPri)(13) (Pr-i = 2-propyl) with Ln = Nd (1) and Gd (2) were synthesized by metathesis of LnCl(3) and KOPri, in combination with stoichiometric hydrolysis, in 2-propanol-containing solvents. E

  • 20. Larhed, M
    et al.
    Hallberg, A
    Microwave-assisted high-speed chemistry: a new technique in drug discovery2001In: Drug Discovery Today, ISSN 1359-6446, E-ISSN 1878-5832, Vol. 6, no 8, p. 406-416Article, review/survey (Refereed)
    Abstract [en]

    In both lead identification and lead optimization processes there is an acute need for new organic small molecules. Traditional methods of organic synthesis are orders of magnitude too slow to satisfy the demand for these compounds. The fields of combinatorial and automated medicinal chemistry have been developed to meet the increasing requirement of new compounds for drug discovery; within these fields, speed is of the essence. The efficiency of microwave flash-heating chemistry in dramatically reducing reaction times (reduced from days and hours to minutes and seconds) has recently been proven in several different fields of organic chemistry. We believe that the time saved by using focused microwaves is potentially important in traditional organic synthesis but could be of even greater importance in high-speed combinatorial and medicinal chemistry.

  • 21.
    Larsson, Michael
    et al.
    Mittuniversitetet i Sundsvall.
    Högberg, Hans-Erik
    Mittuniversitetet.
    Diastereoselective addition of methylmetal reagents to 2-methylaldehydes.2001In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 57, no 35, p. 7541-7548Article in journal (Refereed)
    Abstract [en]

    The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-butyl moiety of high diastereomeric purity is described. These compounds can serve as potential building blocks for the preparation of several kinds of natural products. The diastereoselective addition of a number of methylmetal derivatives to three 3-substituted 2-methylaldehydes in various solvents was studied. An excellent diastereomeric. ratio (95:5 anti-Cram/Crain) was obtained with 2-methyl-3-(phenylsulfanyl)propanal (5) and Me2Zn in the presence of TiCl4.

  • 22.
    Larsson, Michael
    et al.
    Mittuniversitetet i Sundsvall.
    Nguyen, Ba - Vu
    Mittuniversitetet i Sundsvall.
    Högberg, Hans -Erik
    Mittuniversitetet i Sundsvall.
    Hedenström, Erik
    Mittuniversitetet i Sundsvall.
    Syntheses of the sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol, including the (2S,3S,7S,11R) and (2S,3S,7S,11S) stereoisomers identified as pheromone precursors in females of the pine sawfly Microdiprion pallipes (Hymenoptera : Diprionidae).: Diprionidae)2001In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 2, p. 353-363Article in journal (Refereed)
    Abstract [en]

    All sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol were synthesised in high stereoisomerical purities (> 95%), for use in the identification of the stereoisomers present in females of the pine sawfly Microdiprion pallipes (Fallen) (Hymenoptera: Diprionidae) as the precursor of the actual sex pheromone (which is the propionate), and also for investigation of the biological activities of the esters. The key step in the syntheses was the coupling of each of the enantiomers of cis-3,4-dimethyl-gamma -butyrolactone with each of the four pure stereoisomers of 1-lithio-2,6-dimethyloctanes. The four corresponding alcohols were obtained by lipase-catalysed (Amano PS) kinetic separation, based on selective acylation of either (2R/S,6S)- or (2R/S,GR)-2,6-dimethyl-1-octanol (obtained from the optically pure enantiomers of citronellal). Additionally, a mixture of the 16 possible stereoisomers of 3,7,11-trimethyl-2-tridecanol was also prepared.

  • 23.
    Ledung, G.
    et al.
    Mälardalen University, School of Sustainable Development of Society and Technology.
    Bergkvist, M.
    Mälardalen University, School of Sustainable Development of Society and Technology.
    Quist, A.P.
    Uppsala University, Sweden.
    Gelius, U.
    Uppsala University, Sweden.
    Carlsson, J.
    Uppsala University, Sweden.
    Oscarsson, S.
    Uppsala University, Sweden.
    Novel method for preparation of disulfides on silicon2001In: Langmuir, ISSN 0743-7463, Vol. 17, no 2, p. 6056-6058Article in journal (Refereed)
    Abstract [en]

    This work describes an efficient novel method to incorporate reactive disulfide bonds onto a silica surface under mild reaction conditions. The reactive thiol groups introduced onto the silicon surface in the first reaction step will be oxidized but easily converted into highly reactive thiopyridyl groups, which can therefore easily be utilized for further organic synthesis involving thiol-containing molecules. This is done in a way that yields approximately a monolayer of reactant on the surface, thereby not adding to the roughness of the surface, of special importance, for instance, for single molecule interaction studies.

  • 24.
    MacMillar, Susanna
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Kinetic Isotope Effects Studies of Dimethylindene Isomerization2001Report (Other scientific)
  • 25. Macsári, István
    Application of π-allylpalladium chemistry to the synthesis and transformation of allylsilanes2001Doctoral thesis, comprehensive summary (Other academic)
  • 26.
    Nicholls, Ian A.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Adbo, Karina
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Per-Ola
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Ankarloo, Jonas
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Hedin-Dahlström, Jimmy
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Jokela, Päivi
    University of Kalmar, School of Communication and Design.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Olofsson, Linus
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Rosengren-Holmberg, Jenny
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Shoravi, Siamak
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Wikman, Susanne
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Can we rationally design molecularly imprinted polymers?2001In: Analytica Chimica Acta, Vol. 435, no 1, p. 9-18Article in journal (Refereed)
  • 27. Nilsson, P
    et al.
    Larhed, M
    Hallberg, A
    Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a Heck triarylation process2001In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 123, no 34, p. 8217-8225Article in journal (Refereed)
    Abstract [en]

    This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled triand diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.

  • 28.
    Nordberg, A
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Jelic, V
    Arnaiz, E
    Långström, B
    Almkvist, O.
    Brain functional imaging in early and preclinical Alzheimer's disease2001In: 7th Intl. AC. Conf. S.S.S.B.W.K Iqbal:, p. 153-164Article in journal (Other scientific)
  • 29.
    Nordin, Sofia
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Roth, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tarnai, Tibor
    Alonso, Diego
    Brandt, Peter
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Remote Dipole Effects as a Means to Accelerate [Ru(amino alcohol)]-Catalyzed Transfer Hydrogenation of Ketones2001In: Chem. Eur. J., no 7, p. 1431-1436Article in journal (Refereed)
    Abstract
  • 30. Olofsson, K
    et al.
    Sahlin, H
    Larhed, M
    Hallberg, A
    Regioselective palladium-catalyzed synthesis of beta-arylated primary allylamine equivalents by an efficient Pd-N coordination2001In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 2, p. 544-549Article in journal (Refereed)
    Abstract [en]

    A highly regioselective Heck arylation, utilizing aryl triflates and a palladium/dppf catalytic system, can be performed at the internal, beta -carbon of Boc- and phthalimido-protected allylamines, yielding arylated primary allylamine equivalents. The very high regioselectivity obtained with secondary Boc-protected allylamides is suggested to be caused by an efficient coordination between an anionic nitrogen and palladium. Single-mode microwave irradiation has been utilized to shorten the reaction times and, in the case of Boc-protected allylamides, to improve the yields of two electron-poor aryl triflates.

  • 31.
    Pirinccioglu N, Jia Z S, Thibblin A.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Acid-catalysed aromatization of anthranyl derivatives. A kinetic and thermodynamic study.2001In: Journal of Chemical Society, Perkin Transaction 2, p. 2271-2275Article in journal (Refereed)
  • 32. Rewcastle, G W
    et al.
    Janosik, Tomasz
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones2001In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 57, no 33, p. 7185-7189Article in journal (Refereed)
    Abstract [en]

    The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. to a rational approach to pentathiepino[6,7-b]indoles 5 and 10. Notable amounts of the previously known tetrathiocino[5,6-b:8,7-b ' ]diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2-thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a convenient and clean lithiation route to indoline-2-thione (6) has been developed.

  • 33.
    Rotticci, Didier
    et al.
    KTH, Superseded Departments, Chemistry.
    Ottosson, Jenny
    KTH, Superseded Departments, Biotechnology.
    Norin, Torbjörn
    KTH, Superseded Departments, Chemistry.
    Hult, Karl
    KTH, Superseded Departments, Chemistry.
    Candida Antarctica lipase B: A tool for the preparation of optically active alcohols2001In: Methods in Biotechnology 15: Enzymes in Nonaqueous Solvents, Humana Press, 2001, Vol. 15, p. 261-276Chapter in book (Refereed)
  • 34.
    Seebach D., Alberg M., Arvidsson P., Rueping M., Schreiber J.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    From the bioplymer PHB to biological investigations of unnatural B- and y-peptides2001In: Chimia, no 55 (4), p. 345-353Article in journal (Refereed)
  • 35.
    Seebach D., Reuping M., Arvidsson P., Kimmerlin T., Micuch P., Noti C., Langenegger D., Hoyer D.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Linear peptidaseresistant B2/B3-Di-and a/B3-tetrapeptide derivatives with nanomolar affinities to a human somatostatin receptor preliminary communication2001In: Helvetica Chimica Acta, no 84 (11), p. 3503-3510Article in journal (Refereed)
  • 36.
    Seebach D., Schreiber J., Arvidsson P., Frackenpohol J.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    The miraculous CD spectra (and secondary structures?) of B-peptides as they grow longer2001In: Helvetica Chimica Acta, no 84 (2), p. 271-279Article in journal (Refereed)
  • 37. Vallin, K S A
    et al.
    Larhed, M
    Hallberg, A
    Aqueous DMF-potassium carbonate as a substitute for thallium and silver additives in the palladium-catalyzed conversion of aryl bromides to acetyl arenes2001In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 12, p. 4340-4343Article in journal (Refereed)
    Abstract [en]

    Highly selective palladium-catalyzed internal alpha -arylations of alkyl vinyl ethers with aryl and heteroaryl bromides were conveniently conducted in aqueous DMF with potassium carbonate as base and with DPPP as bidentate ligand. The corresponding acetyl arene products were, after hydrolysis, isolated in good to excellent yields. This Heck reaction procedure does not require toxic thallium or expensive silver salt additives, is promoted by water, and is suggested to proceed via charged organopalladium intermediates. Single-mode microwave irradiation was utilized in one example to shorten the reaction time.

  • 38. Witt, A
    et al.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Total syntheses of the benzodiazepine alkaloids circumdatin F and circumdatin C2001In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 8, p. 2784-2788Article in journal (Refereed)
    Abstract [en]

    Total syntheses of circumdatin F and circumdatin C, which both possess a 3H-quinazolin-4-one as well as a 1,4-benzodiazepin-5-one moiety, are described. A tripeptide derivative was synthesized as a key intermediate and dehydrated to a benzoxazine by reaction with triphenylphosphine, iodine, and a tertiary amine. The natural products were attained via rearrangements to an amidine intermediate, deprotection with 45% HBr in acetic acid, and cyclization on silica gel.

  • 39.
    Yngve, Ulrika
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preclinical PET Platform.
    Khan, Tanweera Shaheena
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Medical Sciences. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preclinical PET Platform.
    Bergström, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preclinical PET Platform.
    Långstrom, Bengt
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preclinical PET Platform.
    Labelling of octreotide using Br-76-prosthetic groups2001In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 44, no 8, p. 561-573Article in journal (Refereed)
    Abstract [en]

    A method for labelling the octapeptide octreotide (D-Phe-Cys-Phe-D-TrpLys-Thr-Cys-Thr(ol)) with the positron emitting Br-76 (T-1/2 = 16 h) is presented. epsilon -Boc-protected octreotide was conjugated to N-succinimidyl 4-[Br-76]bromobenzoate 1 and N-succinimidyl 5-[Br-76]bromo-3-pyridinecarboxylate 3 using microwave heating. The conjugates 4 and 5 were isolated in 50-55% radiochemical yield after the removal of the protecting Boc-group. Compound 3 was synthesised from the corresponding trimethylstannyl-precursor in 25% radiochemical yield. The synthesis of methyl-4-[Br-76] bromobenzimidate 8 in 40% radiochemical yield from the precursor methyl -4-trimethylstannylbenzimidate is also described. Experiments were performed to react 8 with Boc-octreotide but no product was obtained. The binding-properties of Br-76-conjugates 4 and 5 to meningiomas were investigated using frozen section autoradiography. Compound 5 showed better binding properties than 4.

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