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  • 1
    Electronic Resource
    Electronic Resource
    Photoinduced Double Addition of Acetylene to 3-Oxocyclopent-1-ene-1-carbonitrile or 3-oxocyclopent-1-enyl acetate leading to 2,3-dihydro-1H-inden-1-one and other rearranged products (1988)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 71 (1988), S. 1608-1615 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: UV Irradiation of 3-oxocyclopent-1-enyl acetate (17) and acetylene in MeCN at 0° gives, besides the product of normal enone-alkyne [2 + 2] cycloaddition (cis-4-oxobicyclo[3.2.0] hept-6-en-1-yl acetate, 18) and its product of oxa-di-π-methane rearrangement (5-oxotricyclo[4.1.0.02,7]hept-2-yl acetate, 19), unexpected products of further addition of a molar equivalent of acetylene. These are indanone ( = 2,3-dihydro-1H-inden-1-one, 16), in 21% yield, cis-1-cisoid-1,2-cis-2- (20) and cis-1-transoid-1,2-cis-2-7-oxotricyclo[4.3.0.02,5]non-3-en-1-yl acetate (21), 4-oxo-7-‘exo’-vinyltricyclo[3.2.0.02,6]hept-2-yl acetate (22), cis-4-oxo-6-‘endo’- (23) and cis-4-oxo-6-‘exo’-vinylbicyclo[3.2.0]hept-1-yl acetate (24), and cis-4-oxo-7-‘exo’-vinylbicyclo[3.2.0]hept-1-yl acetate (25). At least in part, indanone must be formed via intermediates 20 and 21. In fact, on heating a 9:1 mixture 20/21, indanone is obtained quantitatively. With 3-oxocyclopent-1-ene-1-carbonitrile (15) in place of 17, indanone is formed in lower (8%) yield besides much tars.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19880710704
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of the Alleged Natural Monoterpenoid α-SantolinenonePresented by F.P. as part of a lecture at the University of Innsbruck on March 15th, 1984. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1248-1253 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Authentic α-santolinenone ( = (+)-(4R)-1(7)-p-menthen-2-one; (+)-1) is made available for the the first time in 30% overall yield from (+)-(4R)-p-menthene ((+)-2) via the diastereoisomeric allylic alcohols (+)-4a/(+)-4b, which are oxidized to (+)-1 with Ag2CO3/Celite. Yields are good, except for the last stage; indeed, only alcohol (+)-4a, with equatorial OH-group, undergoes oxidation, and (+)-1 is partly substracted via a hetero Diels-Alder dimerization giving a mixture of the diastereoisomeric dihydropyrans (+)-5a/(+)-5b. When Cr(VI) reagents ae used, (+)-4a/(+)-4b mainly give phellandral (6) and carvotanacetone (7), NnO2 reacts too sluggishly with (+)-4a/(+)-4b. A camphor pyrolyzate, previously thought to be 1 must be a different compound, probably 7.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670511
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  • 3
    Electronic Resource
    Electronic Resource
    On the Absolute Configuration of Penlanfuran and Related Sesquiterpenoids of the Sponge Dysidea fragilis from the North-Brittany Sea (1990)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 73 (1990), S. 652-658 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 1,4-addition of vinylmagnesium bromide/CuBr-SMe2 to (+)-(4s)-cryptone ((+)-6) in THF in the presence of Me3SiCI gives the silylenol ether 7 which partly undergoes hydrolysis to ketone 8 on aqueous workup; residual 7 is hydrolyzed with pyridinium p-toluenesulfonate (PyTsOH) to give 8 which is protected in situ with ethylene glycol and then ozonolized to give aldehyde (—)-10. The latter, on addition of 3-lithiofuran followed by dehydration and deprotection with Py TsOH, gives the unnatural (4S)-enantiomer (+)-2 of noroxopenlanfuran. All processes, except 11 → (+)-2, are of good yield. On the basis of previous chemical transformations, this also establishes the (4R)-configuration for penlanfuran ((-)-1) and other sesquiterpenoids of the sponge Dysidea fragilis from the North-Brittany sea. Non viable routes to (±)-noroxoperlanfuran ((±)-2) are also discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19900730314
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  • 4
    Electronic Resource
    Electronic Resource
    The Molecular and Crystal Structure of the Glycopeptide A-40926 Aglycone (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1916-1924 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structure of a glycopeptide antibiotic A-40926 aglycone was investigated by X-ray analysis at -120°. A-40926 crystallises in the orthorhombic space group P212121 with two monomers in the asymmetric unit, a = 21.774(4), b = 28.603(7), c = 29.757(4) Å. ‘Conventional’ direct methods approach failed to solve the structure, but a novel iterative real/reciprocal space procedure was successful. Refinement against 11248 F2 data led to R1 = 13.3% for 6770 F 〉 4σ (F). The two monomers of A-40926 have similar conformations and are bound by antiparallel H-bonds to form a ‘chain’ structure of connecting dimers. The antibiotic molecule possesses a ‘binding pocket’ for the C-terminal carboxy group of the cell-wall protein, which is consisten with suggestions based on NMR data and the recently reported crystal structure of ureido-balhimycin. In A-40926 the monomers are polymerically linked by H-bonds, quite unlike the tight dimer formation observed in ureido-balhimycin.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790714
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  • 5
    Electronic Resource
    Electronic Resource
    Experimental design for parameter estimation from batch culture (1986)
    New York, NY [u.a.] : Wiley-Blackwell
    Biotechnology and Bioengineering 28 (1986), S. 836-841 
    Details
    ISSN: 0006-3592
    Keywords: Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: An experimental design to estimate the parameters in a Monod-type equation from batch culture data was examined. Consideration was given to the design of experiments to estimate accurate values of the parameters. Sequential experimental design with the information index was used for this purpose. With this approach the standard deviation of the parameter values was reduced using simulated batch culture data.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bit.260280610
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  • 6
    Electronic Resource
    Electronic Resource
    Evaluation of chiroptical properties of molecules by asymmetric photochemistry (1991)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 3 (1991), S. 257-262 
    Details
    ISSN: 0899-0042
    Keywords: chiral photochemistry ; excitation transfer ; optical activation ; circular dichroism ; dissymmetry factor ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The physics involved in photochemistry with circularly polarized light, the warnings on its inherent limitations, as well as some examples of application on organic molecules are briefly reviewed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530030408
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  • 7
    Electronic Resource
    Electronic Resource
    Determination by HPLC of adrenalin (E) and of noradrenalin (NE) in certain species of mesopelagic fish in the Strait of MessinaThis paper has not bee peer reviewed (1998)
    New York : Wiley-Blackwell
    Journal of Bioluminescence and Chemiluminescence 13 (1998), S. 311-314 
    Details
    ISSN: 0884-3996
    Keywords: bioluminescence ; adrenalin ; noradrenalin ; photophores ; HPLC ; mesopelagic fish ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: The presence of adrenalin (E) and noradrenalin (NE) was found by HPLC both in the photophores and at other tissue levels of numerous species of mesopelagic fish in The Strait of Messina, with the aim of determining the incidence of these catecholamines in photophores, in light transmission and the eventual presence at other tissue levels. © 1998 John Wiley & Sons, Ltd.
    Additional Material: 3 Ill.
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  • 8
    Electronic Resource
    Electronic Resource
    A comparative study of the purity, enzyme activity, and inactivation by hydrogen peroxide of commercially available horseradish peroxidase isoenzymes A and C (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Biotechnology and Bioengineering 50 (1996), S. 655-662 
    Details
    ISSN: 0006-3592
    Keywords: horseradish peroxidase ; peroxide ; kinetics ; inactivation ; suicide substrate ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: Horseradish peroxidase (HRP) is a commercially important enzyme that is available from a number of supply houses in a variety of grades of purity and isoenzymic combinations. The present article describes a comparative study made on nine HRP preparations. Six of these samples were predominantly composed of basic HRP, pl 8.5, and three of acidic HRP, pl 3.5. Two of the basic preparations were of lower purity than the others. The apparent molar catalytic activity of basic HRP with 0.5 mMABTS and 0.2 mM H2O2 was around 950 s-1 (about 770 s-1 for the less pure samples) and with a 5 mM guaiacol and 0.6 mM H2O2 was about 180 s-1 for all the samples. A similar value (approximately 1000 s-1) was observed for acidic HRP but only at higher concentrations of ABTS (20 mM). With 20 mM guaiacol the molar catalytic activity of the acid isoenzyme was 65 s-1. The apparent KM for ABTS of the acidic isoenzyme was 4 mM whereas for the basic isoenzyme it was 0.1 mM. All the enzymes were inactivated by H2O2 when it was supplied as the only substrate. Under these conditions the partition ratio (r = number of catalytic cycles given by the enzyme before its inactivation), apparent dissociation constant (Kl), and apparent rate constant of inactivation (kinact) were about twice as large for the acidic samples (1350, 2.6 mM, 9 · 10-3 s-1) as for the basic (650, 1.3 mM, 5 · 10-3 s-1). The apparent catalytic constant (kcat) was 3-4 times larger, and the efficiency of catalysis (kcat/Kl) was double for the acidic isoenzyme, but the efficiency of inactivation (kinact/Kl) was similar. The data obtained provide useful information for those using HRP isoenzymes for biotechnological applications (e.g., biosensors, bioreactors, or assays). © 1996 John Wiley & Sons, Inc.
    Additional Material: 3 Ill.
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  • 9
    Electronic Resource
    Electronic Resource
    Effect of bench-scale culture conditions on murine IgG heterogeneity (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Biotechnology and Bioengineering 54 (1997), S. 17-25 
    Details
    ISSN: 0006-3592
    Keywords: hybridoma cell culture ; fermentation ; MAb heterogeneity ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: A stable murine hybridoma cell line, secreting IgG1 antibodies (7H3) against the soluble type I receptor for Tumor Necrosis Factor (sTNF-R1), was cultivated in two different bioreactor systems, a hollow fiber and a stirred tank fermentor, in order to evaluate the effect of culture conditions on antibody structural and functional heterogeneity. Conventional serum-supplemented and serum-free media were chosen for fermentation in stirred tank bioreactor, whereas only serum-supplemented media were used for hollow fiber cultivation. Extent of glycosylation, determined by lectin binding assays, and charge heterogeneity of murine monoclonal antibodies displayed relevant variations according to the fermentation system used. After complete sugars removal by N-glycosidase F treatment, charge heterogeneity were still observed suggesting the occurrence of additional modifications at the protein level. In vitro culture in serum-supplemented media carried out with the hollow fibre system led to higher productivity but greater antibody charge heterogeneity and differences in lectin-binding profile than cultivation in the stirred tank bioreactor.Results cumulatively indicated that hybridoma cultivation methods, but also cultivation time, influence antibody heterogeneity, both in the protein and sugar moieties. © 1997 John Wiley & Sons, Inc. Biotechnol Bioeng 54: 17-25, 1997.
    Additional Material: 7 Ill.
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  • 10
    Electronic Resource
    Electronic Resource
    A new synthesis of (±)-phoracantholide, (±)-dihydrorecifeiolide, and (±)-muscone via α-nitro ketones (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1381-1383 
    Details
    ISSN: 0947-3440
    Keywords: (±)-Phoracantholide ; (±)-Recifeiolide, Dihydro ; (±)-Muscone ; α-Nitro ketones ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cα′ alkylation of α-nitro cycloalkanones 1a-c with methyl iodide at -35 to -70°C in THF/heptane/DMPU/TMDA in the presence of LDA as a base furnished the methylated α-nitro ketones 2a-c. Denitration of 2a, b with Bu3SnH/AIBN in dry benzene afforded the α′-methylated ketones 3a, b, which were converted to (±)-phoracantholide (4a) and (±)-dihydrorecifeiolide (4b), respectively, by the Baeyer-Villiger oxidation. Reduction of 2c with NaBH4 and dehydration of the obtained nitro alkanol 5 with Al2O3/DMAP furnished the corresponding nitro alkene 6. Nef conversion of 6 with sodium hypophosphite and Raney nickel afforded (±)-muscone (7) in good yields.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199507185
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