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  • 1
    Electronic Resource
    Electronic Resource
    Conformational rigidity versus flexibility in a novel peptidic neurokinin A receptor antagonist (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Peptide Science 1 (1995), S. 236-240 
    Details
    ISSN: 1075-2617
    Keywords: Tachykinins ; NK-2 antagonist ; cyclic peptide ; conformation ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Neurokinin A receptor antagonists have been proposed as a new class of drugs for several applications in humans (asthama, intestinal motility, etc.). The rational design, synthesis, structural characterization and biological activity evaluation of a new potent, highly selective, long-lasting, peptide-based receptor antagonist are reported. The structure-activity relationship indicates that the conformational rigidity determines potency, specificity and especially the long life of the molecule in the living body. MEN 10627 is the prototype of a new class of cyclic, peptide-based, neurokinin A receptor antagonists and it is a suitable candidate for clinical testing in humans.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/psc.310010404
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  • 2
    Electronic Resource
    Electronic Resource
    Conformational behaviour of Cα,α-diphenylglycine: folded vs. extended structures in DφG-containing tripeptides (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Peptide Science 4 (1998), S. 21-32 
    Details
    ISSN: 1075-2617
    Keywords: Cα,α-disubstituted amino acids ; crystal structure ; molecular dynamics ; conformation ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structures of three fully protected tripeptides containing the Dφg residue (Cα,α-diphenylglycine) in the central position are reported, namely Z-Gly-Dφg-Gly-OMe (a), Z-Gly-Dφg-Aib-OMe (b) and Z-Aib-Dφg-Aib-OMe (c). The molecular conformations are quite unusual because the Dφg residue adopts a folded conformation in the 310-helical region when the following residue adopts a folded conformation of opposite handedness (peptidesbandc). In contrast, the Dφg residue adopts the more frequently observed fully extended conformation when the following residue adopts a semi-extended conformation (peptidea). These findings are in agreement with the theoretical calculations on Ac-Dφg-Aib-NHCH3 and Ac-Aib-Dφg-NHCH3 also reported in this work. © 1998 European Peptide Society and John Wiley & Sons, Ltd.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Large-scale production of peptides using the solid-phase continuous flow method. Preparative synthesis of the novel tachykinin antagonist MEN 10627 (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Peptide Science 3 (1997), S. 224-230 
    Details
    ISSN: 1075-2617
    Keywords: large-scale peptide synthesis ; SPPS ; continuous flow ; Macrosorb ; Neurokinin A receptor antagonist ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The large-scale solid-phase continuous flow synthesis of the bicyclic peptide MEN 10627, a new potent Neurokinin A receptor antagonist, is described using the Fmoc-polyamide method on both Macrosorb 125 and Macrosorb 250 resin. A new synthesizer designed in-house was realized by assembling Whitey valves and a Waters pump in order to allow small-scale (0.0001 mol; 1×10 cm Omnifit columns) synthetic studies which were strongly predictive of the conditions required for large-scale (0.01-0.10 mol; 3.6 or 4.9×46 cm Büchi columns) production, performed on the same apparatus. ©1997 European Peptide Society and John Wiley & Sons, Ltd.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Large-scale production of peptides using the solid phase continuous flow method. Part 2cf. J. Peptide Sci. 3, 224-230 (1997) for part 1.: preparative synthesis of a 26-mer peptide thrombin inhibitor (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Peptide Science 4 (1998), S. 327-334 
    Details
    ISSN: 1075-2617
    Keywords: large-scale peptide synthesis ; continuous flow ; macrosorb ; hindered sequence ; thrombin inhibitor ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A preparative method for the preparation of large peptides is described. An advantageous theoretical weight of peptide/weight of starting resin ratio (tPw/Rw) of about 0.3 was successfully experimented. The esterification of the first amino acid was realized with a racemization of less than 1%. The study of the coupling conditions led to the use of a diluted acylating mixture that allowed a 56% consumption of the amino acid derivatives (percentage use of amino acids) introduced in the synthesis. The cost analysis of the synthesis showed that the recovery of the amino acid derivatives was not worthwhile. © 1998 European Peptide Society and John Wiley & Sons, Ltd.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Use of capillary gas chromatography/sensory analysis as an additional tool for sampling technique comparison in peach aroma analysis (1995)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 18 (1995), S. 309-314 
    Details
    ISSN: 0935-6304
    Keywords: Sensory analysis ; Headspace analysis ; Solvent extraction ; Volatile substances ; Peach fruit ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Capillary GC/sensory analysis was used to judge if dynamic headspace on sliced pulp and on intact fruit, and solvent extraction could collect the “character impact” and the “contributory” aroma compounds in peaches. Capillary GC/sensory data showed that the headspace techniques selectively recovered the “contributory” volatile compounds, which are strictly related to the characteristic odor of the various peach cultivars, whereas solvent extraction better quantified the “character impact” compounds (lactones).
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240180509
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesen der diastereoisomeren Caparrapioxide (1976)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 59 (1976), S. 1158-1168 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses of Diastereoisomeric Caparrapi oxides.Two pathways have been developed for the synthesis of caparrapi oxide from the dihydroionones. The four diastereoisomeric racemates and their dehydro- and dihydro-derivatives are described. NMR. spectra indicate that the sesquiterpene ethers having cis-fused rings exist in two different conformations.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19760590419
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  • 7
    Electronic Resource
    Electronic Resource
    Hemoprotein Models Based on a Covalent Helix-Heme-Helix Sandwich: 1. Design, Synthesis, and Characterization (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 340-349 
    Details
    ISSN: 0947-6539
    Keywords: helical structures ; heme proteins ; iron ; peptides ; synthesis design ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In this paper we describe the design, synthesis, and spectroscopic characterization of a covalent helix-heme-helix sandwich named FeIII mimochrome I. It contains deuterohemin bound through both propionyl groups to two identical N-and C-terminal protected nonapeptides as α-helical scaffolds. Each peptide moiety bears a His residue in the central position, which acts as axial ligand to the metal ion. The newly developed synthetic strategy is based on a combination of solution and solid-phase methodologies. It represents a powerful method for obtaining a large variety of analogues containing two symmetric or unsymmetric peptide chains covalently bound to the deuteroporphyrin ring. UV/Visible spectroscopic characterization in buffered 2,2,2-trifluoroethanol/water solution proves low-spin bis(his-tidine) iron(III) coordination; circular dichroism (CD) measurements show an α-helical conformation for the peptide moieties. Thus, all the data are in agreement with the designed hypothetical model regarding both the iron(III) coordination and the peptide chain structural organization.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030305
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  • 8
    Electronic Resource
    Electronic Resource
    Hemoprotein Models Based on a Covalent Helix-Heme-Helix Sandwich: 2. Structural Characterization of CoIII Mimochrome I δ and δ Isomers (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 350-362 
    Details
    ISSN: 0947-6539
    Keywords: cobalt ; helical structures ; heme proteins ; NMR spectroscopy ; por-phyrinoids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: FeIII mimochrome I is the prototype of a new class of hemoprotein models characterized by a covalent helix-heme-helix sandwich. It contains deuterohemin bound through two propionyl groups to two identical N- and C-terminal protected α-helical nonapeptides, each of which bears a His residue (a potential axial lig-and of the iron ion) in the central position. In order to understand better the three-dimensional structure of FeIII mimochrome I and its correlation with spectral properties, we have characterized the fully diamagnetic parent compound CoIII mimochrome I by UV/visible, CD, and NMR spectroscopy, coupled with conformational energy calculations. CoIII mimochrome I is a highly water-soluble compound present in solution as two isomers, which slowly interconvert only at very low pH values. These isomers were isolated and separately characterized. Their UV/visible spectral properties are very similar, while their CD spectral properties differ markedly in both the far UV and Soret regions. The isomers were identified by 1H NMR spectroscopy as diastereomers of the δ and δ type. This is the first example of an accurate three-dimensional structure determination in solution of a hemoprotein mimetic that allows a straightforward correlation between structure and spectral properties.
    Additional Material: 13 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030306
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  • 9
    Electronic Resource
    Electronic Resource
    A Modified Cyclodextrin with a Fully Encapsulated Dansyl Group: Self-Inclusion in the Solid State and in Solution (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 373-381 
    Details
    ISSN: 0947-6539
    Keywords: crystal structure ; cyclodextrins ; dansyl derivatives ; fluorescent sensors ; self-inclusion ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A monofunctionalized β-cyclodextrin containing a dansyl moiety, 6- deoxy- 6 - N - ( N′- (5- dimethylamino - 1 - naphthalenesulfonyl)diaminoethane) - β-cyclodextrin (CD-en-DNS, 2), was synthesized and its crystal structure determined. It was shown that the dansyl group is fully encapsulated within the cyclodextrin cavity, with the dimethylamino and sulfonyl groups emerging from opposite sides. The shape of the cavity is considerably flattened, since O(4)-O(4) distances parallel to the naphtalene ring were found to be longer than the others. The conformation of the diaminoethane linker was found to be determined by the inclusion of the dansyl group and by a hydrogen bond between the sulfonamide NH and one of the O(6)-H groups on the cyclodextrin rim. The self-inclusion features of the aromatic moiety were found to be consistent with the solution data: 1H NMR ROESY spectra suggested that the orientation of the dansyl moiety observed in the solid state was retained in aqueous solution; the circular dichroism spectrum was consistent with an axial complexation model. Fluorescence spectra showed that the inclusion of the dansyl group in the cyclodextrin cavity considerably increases the quantum yield: time-resolved fluorescence experiments showed the presence of a long-lifetime component (16.1 ns), which was attributed to the included fluorophore. The ability of 2 to act as a fluorescence sensor was evaluated by the addition of several guests of different shape: fluorescence intensity was lowered, especially upon addition of adamantanecarboxylic acid. All the data obtained were consistent with the model of the in-out movement of the dansyl group from the self-included conformation observed in the solid state to a position more exposed to the bulk solvent. Copper(II) was shown to enhance the difference in the fluorescence of 2 in the presence of guests by additional static quenching.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19960020404
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  • 10
    Electronic Resource
    Electronic Resource
    β-Alanyl-β-alanine in cyclic β-turned peptides (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1181-1188 
    Details
    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In the present paper we describe the synthesis, purification, and single crystal x-ray analysis of the cyclic pentapeptide cyclo-(L-Pro-L-Pro-L-Phe-β-Ala-β-Ala). The peptide was synthesized by classical solution methods and the cyclization of the free pentapeptide was accomplished in good yields in diluted methylenechloride solution using N,N-dicyclohexylcarbodiimide. The compound crystallizes in the monoclinic space group P21 from hot water with five solvent molecules. The Pro1-Pro2 peptide bond is cis and the molecular conformation is stabilized by an intramolecular hydrogen bond between the CO group of the β-Ala5 and the NH of the Phe3 residue. The Pro1-Pro2 segment occupies the relative positions 2 and 3 of a type VIa β-turn, while the L-phenylalanyl-β-alanyl-β-alanine segment is incorporated in a C13-like ring structure. The crystal packing is characterized by a network of 11 intermolecular hydrogen bonds involving all the remaining CO, NH, and the water molecules.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bip.360311006
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