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  • 1
    Electronic Resource
    Electronic Resource
    Enkephalin analogues containing β-naphthylalanine at the fourth position (1990)
    New York : Wiley-Blackwell
    Biopolymers 29 (1990), S. 179-196 
    Details
    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: To examine the importance of the aromatic side chains of enkephalin on opiate activity, we report the synthesis and conformational analysis of a series of analogues related to enkephalin with β-naphthylalanine in place of phenylalanine at the fourth position. Three linear analogues (Tyr-D-Ala-Gly-(L and D)-β Nal(1)-Leu-NH2 and Tyr-D-Ala-Gly-β Nal(2)-Leu-NH2) were initially synthesized to examine the effect of the substitution on biological activity. The increased activity of these peptides at the μ-opiate receptor, compared to native Leu-enkephalin, prompted us to examine the more conformational constrained analogues, Tr-c[D-A2bu-Gly-(L and D)-β Nal(1)-Leu], incorporating a α,γ-diaminobutyric acid at the second position and cyclization to the carboxylic end of the leucine. These two cyclic analogues provide insight into the necessity for the L chirality of the aromatic residue at position 4. The Tyr-c[D-A2bu-Gly-L-β Nal(1)-Leu] analogue is highly potent and displays a slight preference for the μ receptor. The conformational analysis indicates that despite the high flexibility of the tyrosine side chain, the aromatic rings of the tyrosine and naphthylalanine are relatively distant from each other. The presence of two intramolecular hydrogen bonds help maintain the conformation of the 14-membered backbone ring that keeps the side chains directed away from each other. These findings are in agreement with our model of an extended structure required for μ selectivity and a folded form with close aromatic ring placement for δ selectivity.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bip.360290123
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  • 2
    Electronic Resource
    Electronic Resource
    Photocycloadditions of 2-(trimethylsilyloxy)-1,3-butadiene to 2-cycloalkenones. Access to the basic pentalenolactone skeletonPreliminary communication: [1]. (1988)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 71 (1988), S. 1392-1398 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The [2 + 2] Photocycloaddition of 2-(trimethylsilyloxy)-1,3-butadiene to a number of 2-cycloalkenones proved to be quite a general reaction leading to good yields of the cycloadducts (Table). This finding is surprising since dienes, in general, are better known as quenchers of enone triplets rather than as photochemical reactants. Both the high substrate concentrations, which can be employed in these cycloadditions, and the remarkable regio and stereoselectivity of the processes qualify them as valuable for syntheses. In a first application, the photoproducts 1a, b were transformed in three steps into a viable precursor 4 of the pentalenolactone-G and -H antibiotics.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19880710603
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  • 3
    Electronic Resource
    Electronic Resource
    Molecular-weight distributions in the thermally initiated emulsion polymerization of styrene (1991)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 192 (1991), S. 405-414 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: In both thermal emulsion polymerization of styrene in the temperature range 60-80 °C, and peroxodisulfate-initiated polymerization at 60 °C, weight-average to number-average molecular-weight ratios (M̄w/M̄n) approach 1,5 when potassium octadecanoate is used as emulsifier. A low activation energy for thermal initiation (≈66,0 kJ/mol) was deduced which may indicate a catalytic effect of the emulsifier during the thermal initiation process. Participation of the emulsifier is probably attributed to a transfer of one of two monomer radicals, produced thermally, to the emulsifier, with subsequent desorption to the aqueous phase, leaving one radical in the polymerization locus.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1991.021920220
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  • 4
    Electronic Resource
    Electronic Resource
    Graft copolymerization of acrylonitrile on starch (1989)
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Letters Edition 27 (1989), S. 433-436 
    Details
    ISSN: 0887-6258
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pol.1989.140271106
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  • 5
    Electronic Resource
    Electronic Resource
    Perfluorinated anion exchange membranes: Preparation and preliminary tests of dialysis (1992)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 30 (1992), S. 1407-1412 
    Details
    ISSN: 0887-624X
    Keywords: radiochemical grafting ; anion exchange membrane ; acid dialysis ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Using the preirradiation technique a kinetic study of the grafting of the 4-vinyl pyridine (V4P) and an aliphatic ammonium monomer (ALAM) onto the copolymer film of ethylene-tetrafluoroethylene (ETFE) has been performed. The influence of dose, temperature, and concentration of monomer, reticular agent, and inhibitor were investigated. The results are discussed on the basis of the interactions between monomer diffusibility and viscosity of the medium. The characteristics of some membranes were determined. Their applicability to the recovery of acid by dialysis is demonstrated.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1992.080300720
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  • 6
    Electronic Resource
    Electronic Resource
    Reactivity of the exocyclic double bond in 4-arylidene-2-phenyl-2-imidazolin-5-ones toward organomagnesium compounds. II (1971)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 313 (1971), S. 594-601 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 4-Arylidene-2-phenyl-2-imidazolin-5-ones 1 react with Grignard reagents in a boiling ether-benzene mixture to yield 4-diarylmethyl derivatives 2 together with their oxidation products 3 and 4. The exocyclic double bond in 5 also undergoes addition reaction with the same reagents to yield 4-triarylmethyl derivatives 6. Alkylation of 2 affords the 4-alkylimidazolones 7 and 8.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19713130406
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  • 7
    Electronic Resource
    Electronic Resource
    The electrical conductivity of cellulose HYPHAN® and its complexes (1993)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 212 (1993), S. 13-18 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Die elektrische Leitfähigkeit (σ) von Cellulose-HYPHAN® und seinen Komplexen mit Cr3+, Mn2+, Mo5+ und Hg2+ wurde im Temperaturbereich 25-510°C bestimmt. Die Aktivierungsenergie wurde aus der Abhängigkeit von log σ von der reziproken Temperatur berechnet. Die Ergebnisse zeigen, daß die Leitfähigkeit mit steigender Temperatur zunimmt und dabei zwei Maxima durchläuft. Das erste Maximum läßt sich dem Wassergehalt zuordnen, während das zweite mit dem thermischen Abbau der Cellulose-Kette zusammenhängt. Die Werte der Aktivierungsenergie lassen darauf schlieäen, daß sich beim Erhitzen die Halbleitereigenschaften der Komplexe verbessern.
    Notes: The electrical conductivity, σ, of cellulose HYPHAN® and its complexes with Cr3+, Mn2+, Mo5+ or Hg2+ was measured from room temperature to 510°C. The activation energy, ΔE, of the samples was calculated from log σ against 1/T curves. The results show that the electrical conductivity increases by temperature with two maximum peaks. The first peak is attributed to the moisture content, while the second one is attributed to the thermal degradation of the cellulose chain. The values of the activation energy indicate that the samples change from low semiconductor to high semiconductor property with heating.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1993.052120102
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  • 8
    Electronic Resource
    Electronic Resource
    Conformational studies of stereoisomeric 14-membered cyclic enkephalin analogues containing 1-naphthyialanine at the fourth position: Chirality effect of leucine at the fifth position on biological activity and receptor selectivity (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 877-898 
    Details
    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In order to study structure-activity relationships of enkephalin-related analogues, we report the biological activity and conformational analysis of four 14-membered cyclic enkephalin analogues with β-(1-naphthyl)alanine in place of phenylalanine at the fourth position, Tyr-c[D-A2bu-Gly-(L and D)-βNal(1)-(L and D)-Leu]. The L-βNal(1)-containing analogues display higher activity at both the μ and δ receptors than the corresponding analogues with the L-Phe residue. In contrast to the linear enkephalins, the cyclic analogues with the D-βNal(1) residue are also active at the μ receptor since the relative spatial arrangement of functional groups required for biological activity is achieved by the constrained nature of the cyclic molecules. A comparison of the findings from the conformational analysis and biological assays establishes that relatively extended structures, in which the two aromatic side chains are oriented in opposite directions with a ∼ 14Å separation, is required for activity at the μ receptor. On the other hand, folded conformations with nearly parallel orientations and a close proximity ( 〈 10Å) of the aromatic rings of the Tyr and βNal(1) residues are required for activity at the δ receptor. It should be noted that the overall structures and thus the biological profiles of the 14-membered cyclic enkephalin analogues are strongly dependent on the conformation of the second residue. The folded conformations with parallel orientation of the two aromatic side chains of Tyr-c [D-A2bu-Gly-L-βNal (1)-D-Leu] is stabilized by an interaction between the Tyr phenolic OH proton and βNal(1) C*O groups. This analogue, which shows the highest activity at both the μ and δ receptors among the four stereoisomers studied, displays an increase of the fraction of the side-chain χ1 = t conformer for the βNal(1) residue. It is concluded that the incorporation of the D-Leu residue at the fifth position increases the relative fraction of the folded conformations with parallel orientation of the aromatic side chains, and hence enhances activity at the δ receptor as compared to the corresponding L-Leu containing analogue.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bip.360310708
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  • 9
    Electronic Resource
    Electronic Resource
    Modifications of the amide bond and conformational constraints in pseudopeptide analogues (1993)
    New York : Wiley-Blackwell
    Biopolymers 33 (1993), S. 1135-1148 
    Details
    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: We have investigated the conformational effects of modifying the amide group in model dipeptides. The N-methyl amide ψ[CO-NMe], N-hydroxy amide ψ[CO-N(OH)], N-amino amide ψ[ CO-N (NH2)], retro amide ψ[ NH-CO], reduced amide in the neutral ψ[CH2-NH] and protonated ψ[CH2-N + H2] state, and hydrazide ψ[CO-NH-NH] have been introduced as surrogates of the amide link in pseudopeptide derivatives of the Pro-Gly or Ala-Gly model dipeptides protected on both termini by an amide group. These compounds have been studied in solution by proton nmr and ir spectroscopy, and in the solid state by x-ray diffraction, giving an extended data set of experimental structural and conformational information on pseudopeptide sequences. The conformational effects depend both on the nature and the position of the modified amide link. Some modifications appear to have no intrinsic conformational induction (N-amino and retro amide), but destabilize any local folded structure by hydrogen-bond breaking. Because of the formation of strong intramolecular interactions, others are capable of stabilizing a β-turn (for example protonated reduced amide), or of inducing a particular local conformation such as a β- or γ-like turn (for example N-hydroxy amide). The particular geometry of the cis N-methyl amide and of the “hydrazino” proline favors the formation of a sharp turn of the main chain. All these structural data are of interest to the design of bioactive peptide mimics. © 1993 John Wiley & Sons, Inc.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bip.360330715
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  • 10
    Electronic Resource
    Electronic Resource
    Farnesyltransferase as a target for anticancer drug design (1997)
    New York : Wiley-Blackwell
    Biopolymers 43 (1997), S. 25-41 
    Details
    ISSN: 0006-3525
    Keywords: Ras ; signal transduction ; farnesyltransferase ; GTPase ; anticancer drug design ; peptidomimetics ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The currently understood function for Ras in signal transduction is in mediating the transmission of signals from external growth factors to the cell nucleus. Mutated forms of this GTP-binding protein are found in 30% of human cancers with particularly high prevalence in colon and pancreatic carcinomas. These mutations destroy the GTPase activity of Ras and cause the protein to be locked in its active, GTP bound form. As a result, the signaling pathways are activated, leading to uncontrolled tumor growth. Ras function in signaling requires its association with the plasma membrane. This is achieved by posttranslational farnesylation of a cysteine residue present as part of the CA1A2X carboxyl terminal tetrapeptide of all Ras proteins. The enzyme that recognizes and farnesylates the CA1A2X sequence, Ras farnesyltransferase (FTase), has become an important target for the design of inhibitors that might be interesting as antitumor agents. Several approaches have been taken in the search for in vivo active inhibitors of farnesyltransferase. These include the identification of natural products such as the chaetomellic and zaragozic acids that mimic farnesylpyrophosphate, bisubstrate transition state analogs combining elements of the farnesyl and tetrapeptide substrates and peptidomimetics that reproduce features of the carboxyl terminal tetrapeptide CA1A2X sequence. This last group of compounds has been most successful in showing highly potent inhibition of FTase and selective blocking of Ras processing in a range of Ras transformed tumor cell lines at concentrations as low as 100 nM. Certain peptidomimetics will also block tumor growth in various mouse models, with apparently few toxic side effects. These results suggest that farnesyltransferase inhibitors hold considerable promise as anticancer drugs in the clinic. © 1997 John Wiley & Sons, Inc. Biopoly 43: 25-41, 1997
    Additional Material: 15 Ill.
    Type of Medium: Electronic Resource
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