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  • 1
    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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    Paper (German National Licenses)
  • 2
    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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  • 3
    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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  • 4
    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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