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Zusammenfassung

Die Zeit nach der ersten Synthese eines Peptidwirkstoffes, des Oxytocins, durch du Vigneaud im Jahre 1953, ist mit mannigfaltigen Bemühungen angefüllt, die präparativen Methoden der Peptidchemie zu vervollkommnen. Stimulierend für diese Bemühungen waren die Fortschritte bei der Isolierung und Strukturaufklärung einer Vielzahl von Naturstoffen mit Peptidstruktur und der Wunsch nach eindeutigen und rationellen Synthesen der neuen biologisch aktiven Substanzen. Mit der Zugänglichkeit von Peptidwirkstoffen durch Synthese wurden eingehende pharmakologische und medizinische Untersuchungen ermcht, die viel zum heutigen Verständnis über die physiologische Bedeutung der verschiedensten Polypeptidwirkstoffe beigetragen haben. In einigen Fällen konnten mit synthetischen Produkten sogar therapeutische Anwendungsmchkeiten erschlossen werden.

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Literaturverzeichnis

  1. Acher, R., J. Chauvet, M. T. Chauvet et D. Crepy: Phylogénie des peptides hormonaux neurohypophysaires. Bull. soc. chim. biol. (Paris) 47, 2279 (1965).

    Google Scholar 

  2. Albertson, N. F.: Synthesis of Peptides with Mixed Anhydrides. Organ. React. 12, 157 (1962).

    CAS  Google Scholar 

  3. Anastasi, A., G. Bertaccini and V. Erspamer: Pharmacological Data on Phyllokinin (Bradykinyl-Isoleucyl-Tyrosine O-Sulphate) and Bradykinyl-Isoleucyl-Tyrosine. Brit. J. Pharmacol. 27, 479 (1966).

    CAS  Google Scholar 

  4. Anderson, G. W. and F. M. Callahan: t-Butyl Esters of Amino Acids and Peptides and their Use in Peptide Synthesis. J. Amer. Chem. Soc. 82, 3359 (1960).

    CAS  Google Scholar 

  5. Anderson, G. W., F. M. Callahan and J. E. Zimmerman: Synthesis of N-Hydroxysuccinimide Esters of Acyl Peptides by the Mixed Anhydride Method. J. Amer. Chem. Soc. 89, 178 (1967).

    CAS  Google Scholar 

  6. Anderson, G. W. and A. C. McGregor: t-Butyloxycarbonylamino Acids and Their Use in Peptide Synthesis. J. Amer. Chem. Soc. 79, 6180 (1957).

    CAS  Google Scholar 

  7. Anderson, G. W., J. E. Zimmerman and F. M. Callahan: The Use of Esters of N-Hydroxysuccinimide in Peptide Synthesis. J. Amer. Chem. Soc. 86, 1839 (1964).

    CAS  Google Scholar 

  8. Anderson, J. C, M. A. Barton, R. A. Gregory, P. M. Hardy, G. W. Kenner, J. K. MacLeod, J. Preston, R. C. Sheppard and J. S. Morley: Synthesis of Gastrin. Nature 204, 933 (1964).

    Google Scholar 

  9. Anderson, J. C, G. W. Kenner, J. K. MacLeod und R. C. Sheppard: Peptides. XXII. Syntheses of Porcine Gastrin I. Tetrahedron Suppl. 8, Part I, 39 (1966).

    Google Scholar 

  10. Aoyagi, H. and N. Izumiya: Studies of Peptide Antibiotics. V. Syntheses of Cyclic Penta-and Decapeptides with the L-Valyl-L-ornithyl-L-leucyl-D-phenyl-alanylsarcosyl Sequence. Bull. Chem. Soc. Japan 39, 1747 (1966).

    CAS  Google Scholar 

  11. Aoyagi, H., T. Kato, M. Ohno, M. Kondo, M. Waki, S. Makisumi and N. Izumiya: Studies on Peptide Antibiotics. III. Cyclo-(L-valyl-L-ornithyl-L-leucyl-D-phenylalanylglycyl)2. Bull. Chem. Soc. Japan 38, 2139 (1965).

    CAS  Google Scholar 

  12. Arakawa, K. and F. M. Bumpus: An Improved Synthesis of Isoleucine5 Angiotensin Octapeptide. J. Amer. Chem. Soc. 83, 728 (1961).

    CAS  Google Scholar 

  13. Arakawa, K., M. Nakatani and M. Nakamura: Purification of Human Angiotensin. Nature 214, 278 (1967).

    CAS  Google Scholar 

  14. Bajusz, S.: A Novel Synthesis of Eledoisin. Acta Chim. Hungar. 42, 383 (1964).

    CAS  Google Scholar 

  15. Bajusz, S. und K. Medzihradszky: Erfahrungen über das Verhalten geschützter Peptide bei der Reaktion mit Natrium in flüssigem Ammoniak. In: G. T. Young (ed.), Peptides. Proc. 5th Europ. Sympos. Oxford 1962, p. 49. Oxford, London, New York, Paris: Pergamon Press. 1963.

    Google Scholar 

  16. Bajusz, S. und K. Medzihradszky: Synthesis and Biological Activity of Corticotropin Fragments. Siehe Lit. 32, p. 209.

    Google Scholar 

  17. Bajusz, S., K. Medzihradszky, Z. Paulay und Zs. Láng: Totalsynthese des menschlichen Corticotropins (αh-ACTH). Acta Chim. Hungar. 52, 335 (1967)

    CAS  Google Scholar 

  18. Beacham, J., P. H. Bentley, R. A. Gregory, G. W. Kenner, J. K. MacLeod and R. C. Sheppard: Human Gastrin: Isolation, Structure and Synthesis: Synthesis of Human Gastrin I. Nature 209, 585 (1966).

    CAS  Google Scholar 

  19. Beacham, J., P. H. Bentley, G. W. Kenner, J. J. Mendive and R. C. Sheppard: Gastrins from Some Mammalian Species. Siehe Lit. 32, p. 235.

    Google Scholar 

  20. Berger, A., J. Noguchi and E. Katchalski: Poly-L-cysteine. J. Amer. Chem. Soc. 78, 4483 (1956).

    CAS  Google Scholar 

  21. Bergmann, M. und L. Zervas: Über ein allgemeines Verfahren der Peptid-synthese. Ber. dtsch. chem. Ges. 65, 1192 (1932).

    Google Scholar 

  22. Bernardi, L.: Synthetic Peptides Related to Physalaemin and Eledoisin. In: E. G. Erdös, N. Back and F. Sicuteri (ed.), Hypotensive Peptides. Proc. Internat. Sympos., Florence 1965, p. 86. New York: Springer, 1966.

    Google Scholar 

  23. Bernardi, L., G. Bosisio, R. de Castiglione and O. Goffredo: Synthesis of Phyllokinin, a Natural Bradykinin Analogue. Experientia 22, 425 (1966).

    CAS  Google Scholar 

  24. Bernardi, L., G. Bosisio, F. Chillemi, G. de Caro, R. de Castiglione, V. Erspamer, A. Glaesser and O. Goffredo: Synthetic Peptides Related to Eledoisin. Experientia 20, 306 (1964).

    CAS  Google Scholar 

  25. Bernardi, L., G. Bosisio, F. Chillemi, G. de Caro, R. de Castiglione, V. Erspamer, A. Glaesser and O. Goffredo: Synthetic Peptides Related to Eledoisin. Experientia 21, 695 (1965).

    CAS  Google Scholar 

  26. Bernardi, L., G. Bosisio, O. Goffredo and R. de Castiglione: Synthesis of Physalaemin. Experientia 20, 490 (1964).

    CAS  Google Scholar 

  27. Bertaccini, G., J. M. Cei and V. Erspamer: Occurrence of Physalaemin in Extracts of the Skin of Physalaemus Fuscumaculatus and its Pharmacological Actions on Extravascular Smooth Muscle. Brit. J. Pharm. Chemotherap. 25, 363 (1965).

    CAS  Google Scholar 

  28. Bethge, H. und F. A. Gries: Untersuchungen über die adrenocorticotrope Wirkung von β1–24-Corticotropin beim Menschen. Arch. exp. Pathol. Pharma-kol. 254, 425 (1966).

    CAS  Google Scholar 

  29. Beyerman, H. C. and J. S. Bontekoe: The t-Butoxy Group, a Novel Hydro-xyl-Protecting Group for Use in Peptide Synthesis with Hydroxy-Amino Acids. Rec. trav. chim. Pays-Bas 81, 691 (1962).

    CAS  Google Scholar 

  30. Beyerman, H. C. and J. S. Bontekoe: Synthesis of the C-Terminal Tetrapeptide Sequence Derived from Glu-cagon. Rec. trav. chim. Pays-Bas 81, 699 (1962).

    CAS  Google Scholar 

  31. Beyerman, H. C, J. S. Bontekoe and A. C. Koch: A Synthesis of Oxytocin. Rec. trav. chim. Pays-Bas 78, 935 (1959).

    CAS  Google Scholar 

  32. Beyerman, H. C, A. van de Linde and W. Maassen van den Brink (ed.): Peptides. Proc. 8th Europ. Peptide Sympos. Noordwijk, Netherl. 1966. Amsterdam: North-Holland Publ. Co. 1967.

    Google Scholar 

  33. Bodanszky, M. and V. du Vigneaud: An Improved Synthesis of Oxytocin. J. Amer. Chem. Soc. 81, 2504 (1

    CAS  Google Scholar 

  34. Bodanszky, M. and V. du Vigneaud: A Method of Synthesis of Long Peptide Chains Using a Synthesis of Oxytocin as an Example. J. Amer. Chem. Soc. 81, 5688 (1

    CAS  Google Scholar 

  35. Bodanszky, M., J. Meienhofer and V. du Vigneaud: Synthesis of Lysine-vasopressin by the Nitrophenyl Ester Method. J. Amer. Chem. Soc. 82, 3195 (1960).

    CAS  Google Scholar 

  36. Bodanszky, M. and M. A. Ondetti: Peptide Synthesis. New York: J. Wiley and Sons. 1966.

    Google Scholar 

  37. Bodanszky, M., M. A. Ondetti, C. A. Birkhimer and P. L. Thomas: Synthesis of Arginine-Containing Peptides through their Ornithine Analogs. Synthesis of Arginine Vasopressin, Arginine Vasotocin, and L-Histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycine. J. Amer. Chem. Soc. 86, 4452 (1964).

    CAS  Google Scholar 

  38. Bodanszky, M., M. A. Ondetti, S. D. Levine, V. L. Narayanan, M. von Saltza, J. T. Sheehan, N. J. Williams and E. F. Sabo: Synthesis of a Hepta-cosapeptide Amide with the Hormonal Activity of Secretin. Chem. and Ind. 1966, 1757.

    Google Scholar 

  39. Bodanszky, M. and D. Perlman: Are Peptide Antibiotics Small Proteins? Nature 204, 840 (1964).

    CAS  Google Scholar 

  40. Bodanszky, M. and J. T. Sheehan: Active Esters and Resins in Peptide Synthesis. Chem. and Ind. 1964, 1423.

    Google Scholar 

  41. Bodanszky, M., M. Szelke, E. TömörkÉny and E. Weisz: Peptide Synthesis by Aminolysis of Active Esters. Chem. and Ind. 1955, 1517.

    Google Scholar 

  42. Boissonnas, R. A.: Selectively Removable Amino Protective Groups Used in the Synthesis of Peptides. Adv. Organ. Chem. 3, 159 (1963).

    CAS  Google Scholar 

  43. Boissonnas, R. A., St. Guttmann, R. L. Huguenin, P.-A. Jaquenoud et Ed. Sandrin: Synthèse de la L-histidyl-L-phénylalanyl-L-arginyl-L-trypto-phanyl-glycyl-ε-CBO-L-lysyl-L-prolyl-L-valylamide. Helv. Chim. Acta 41, 1867 (1958).

    CAS  Google Scholar 

  44. Boissonnas, R. A., St. Guttmann et P.-A. Jaquenoud: Synthèse de la L-argi-nyl-L-prolyl-L-prolyl-glycyl-L-phénylalanyl-L-séryl-L-prolyl-L-phénylalanyl-L-ar-ginine, un nonapeptide présentant les propriétés de la bradykinine. Helv. Chim. Acta 43, 1349 (1960).

    CAS  Google Scholar 

  45. Boissonnas, R. A., St. Guttmann, P.-A. Jaquenoud et J.-P. Waller: Une nouvelle synthèse de l’oxytocine. Helv. Chim. Acta 38, 1491 (1955).

    CAS  Google Scholar 

  46. Boissonnas, R. A., St. Guttmann, J.-P. Waller and P.-A. Jaquenoud: Synthesis of a Polypeptide with ACTH-like Structure. Experientia 12, 446 (1956).

    CAS  Google Scholar 

  47. Boissonnas, R. A. et R. L. Huguenin: Synthèse de la Lys8-oxytocine (lysine-vasotocine) et nouvelle synthèse de la lysine-vasopressine. Helv. Chim. Acta 43, 182 (1960).

    CAS  Google Scholar 

  48. Bruckner, V. and K. Medzihradszky (ed.): Proc. 7th Europ. Peptide Sympos., Budapest 1964; Acta Chim. Hungar. 44 (1965).

    Google Scholar 

  49. Callahan, F. M., G. W. Anderson, R. Paul and J. E. Zimmerman: The Tertiary Butyl Group as a Blocking Agent for Hydroxyl, Sulfhydryl and Amido Functions in Peptide Synthesis. J. Amer. Chem. Soc. 85, 201 (1963).

    CAS  Google Scholar 

  50. Carpenter, F. H. and D. T. Gish: The Application of P-Nitrobenzyl Chloro-formate to Peptide Synthesis. J. Amer. Chem. Soc. 74, 3818 (1952).

    CAS  Google Scholar 

  51. Chillemi, F.: Sintesi della fisalemina, un endecapeptide biologicamente attivo del „Physalaemus fuscumaculatus“. Gazz. chim. ital. 95, 402 (1965).

    CAS  Google Scholar 

  52. Chung, D. and C. H. LI: The Synthesis of D-Tryptophanyl-D-arginyl-D-phenylalanyl-D-histidyl-D-glutamie Acid and its Effect on Melanotropic Activity. Biochim. Biophys. Acta 136, 570 (1967).

    CAS  Google Scholar 

  53. Consden, R., A. H. Gordon, A. J. P. Martin and R. L. M. Synge: Gramicidin S: the Sequence of the Amino-acid Residues. Biochem. J. 41, 596 (1947).

    CAS  Google Scholar 

  54. Determann, H.: Gelchromatographie. Gelfiltration, Gelpermeation, Molekülsiebe. Berlin, Heidelberg, New York: Springer-Verl. 1967.

    Google Scholar 

  55. Doepfner, W.: Biological Characterization of a New and Highly Potent Synthetic Analogue of Corticotrophin. Experientia 22, 527 (1966).

    CAS  Google Scholar 

  56. Du Vigneaud, V. and O. K. Behrens: A Method for Protecting the Imidazole Ring of Histidine During Certain Reactions and its Application to the Preparation of L-Amino-N-Methylhistidine. J. Biol. Chem. 117, 27 (1937).

    Google Scholar 

  57. Du Vigneaud, V., D. T. Gish, P. G. Katsoyannis and G. P. Hess: Synthesis of the Pressor-Antidiuretic Hormone, Arginine-Vasopressin. J. Amer. Chem. Soc. 80, 3355 (1958).

    Google Scholar 

  58. Du Vigneaud, V., C. Ressler, J. M. Swan, C. W. Roberts, P. G. Katsoy-annis and S. Gordon: The Synthesis of an Octapeptide Amide with the Hormonal Activity of Oxytocin. J. Amer. Chem. Soc. 75, 4879 (1953).

    Google Scholar 

  59. Fontana, A., F. Marchiori, L. Moroder and E. Scoffone: New Removal Conditions of Sulfenyl Groups in Peptide Synthesis. Tetrahedron Letters 1966, 2985.

    Google Scholar 

  60. Fridkin, M., A. Patchornik and E. Katchalski: A Synthesis of Cyclic Peptides Utilizing High Molecular Weight Carriers. J. Amer. Chem. Soc. 87, 4646 (1965).

    CAS  Google Scholar 

  61. Geiger, R., K. Sturm und W. Siedel: Synthese eines biologisch aktiven Tri-cosapeptidamids mit der Aminosäuresequenz 1–23 des Corticotropins (ACTH). Chem. Ber. 97, 1207 (1964).

    CAS  Google Scholar 

  62. Geiger, R., K. Sturm, G. Vogel und W. Siedel: Synthetische Analoga des Corticotropins. Zur Bedeutung der aminoterminalen Sequenz Ser-Tyr-Ser für die adrenocorticotrope Wirkung. Z. Naturforsch. 19b, 858 (1964).

    CAS  Google Scholar 

  63. Greenstein, J. P. and M. Winitz: Chemistry of the Amino Acids. New York-London: J. Wiley and Sons. 1961.

    Google Scholar 

  64. Gregory, H., P. M. Hardy, D. S. Jones, G. W. Kenner and R. C. Shep-pard: The Antral Hormone Gastrin. Nature 204, 931 (1964).

    CAS  Google Scholar 

  65. Gross, F.: Angiotensin. Arch. exp. Pathol. Pharmakol. 245, 196 (1963).

    CAS  Google Scholar 

  66. Guttmann, St.: On the Use of the Tosyl Group for the Protection of Basic Amino-Acids. In: G. T. Young (ed.), Peptides. Proc. 5th Europ. Sympos. Oxford 1962, p. 41. Oxford-London-New York-Paris: Pergamon Press. 1963.

    Google Scholar 

  67. Guttmann, St.: Synthèse du glutathion et de l’oxytocine à l’aide d’un nouveau groupe protecteur de la fonction thiol. Helv. Chim. Acta 49, 83 (1966).

    Google Scholar 

  68. Guttmann, St. et R. A. Boissonnas: Synthèse de l’α-mélanotropine (α-MSH) de Porc. Helv. Chim. Acta 42, 1257 (1959).

    Google Scholar 

  69. Guttmann, St. et R. A. Boissonnas: Synthèse de la Sér4-oxytocine, de l’Ala4-oxytocine, de la Sér5-oxytocine et de l’Ala5-oxytocine. Helv. Chim. Acta 46, 1626 (1963).

    Google Scholar 

  70. Guttmann, St. and J. Pless: On the Protection of the Guanidino Group of Arginine. Acta Chim. Hungar. 44, 23 (1965).

    Google Scholar 

  71. Guttmann, St., J. Pless and R. A. Boissonnas: Synthesis of Peptides Related to ACTH. Acta Chim. Hungar. 44, 141 (1965).

    CAS  Google Scholar 

  72. — Synthesis of a Highly Active Peptide Related to Corticotropin. Siehe Lit. 32, p. 221.

    Google Scholar 

  73. Habermann, E.: Strukturaufklärung kininliefernder Peptide aus Rinderserum-Kininogen. Arch. exp. Pathol. Pharmakol. 253, 474 (1966).

    CAS  Google Scholar 

  74. Habermann, E. und J. Jentsch: Über die Struktur des toxischen Bienengift-peptids Melittin und deren Beziehung zur pharmakologischen Wirkung. Arch. exp. Pathol. Pharmakol. 253, 40 (1966).

    Google Scholar 

  75. Handford, B. O., J. H. Jones, G. T. Young and T. F. N. Johnson: Amino Acids and Peptides. XXIV. The Use of Esters of I-Hydroxypiperidine and of Other NN-Dialkylhydroxylamines in Peptide Synthesis and as Selective Acylating Agents. J. Chem. Soc. (London) 1965, 6814.

    Google Scholar 

  76. Haux, P., H. Sawerthal und E. Habermann: Sequenzanalyse des Bienengift-Neurotoxin (Apamin) aus seinen tryptischen und chymotryptischen Spaltstücken. Z. physiol. Chem. 348, 737 (1967).

    CAS  Google Scholar 

  77. Heaton, G. S., H. N. Rydon and J. A. Schofield: Polypeptides. III. The Oxidation of Some Peptides of Cysteine and Glycine. J. Chem. Soc. (London) 1956, 3157.

    Google Scholar 

  78. Heller, H.: Neurohypophyseal Hormones. In: U. S. v. Euler and H. Helle (ed.): Comparative Endocrinology, vol. 1, p. 25. New York-London: Academic Press. 1963.

    Google Scholar 

  79. Hofmann, K. and P. G. Katsoyannis: Synthesis and Function of Peptides of Biological Interest. In: H. Neurath (ed.), The Proteins: Composition, Structure and Function, vol. 1, p. 53. New York-London: Academic Press. 1963.

    Google Scholar 

  80. Hofmann, K., R. D. Wells, H. Yajima and J. Rosenthaler: Studies on Polypeptides. XXVII. Elimination of the Methionine Residue as an Essential Functional Unit for in vivo Adrenocorticotropic Activity. J. Amer. Chem. Soc. 85, 1546 (1963).

    CAS  Google Scholar 

  81. Hofmann, K., H. Yajima, T.-Y. Liu, N. Yanaihara, C. Yanaihara and J. L. Humes: Studies on Polypeptides. XXV. The Adrenocorticotropic Potency of an Eicosapeptide Amide Corresponding to the N-Terminal Portion of the ACTH Molecule; Contribution to the Relation between Peptide Chain-Length and Biological Activity. J. Amer. Chem. Soc. 84, 4481 (1962).

    CAS  Google Scholar 

  82. Hofmann, K., H. Yajima and E. T. Schwartz: Studies on Polypeptides. XVII. The Synthesis of Three Acyltridecapeptide Amides Possessing a High Level of Melanocyte-expanding Activity in vitro. J. Amer. Chem. Soc. 82, 3732 (1960).

    CAS  Google Scholar 

  83. Hofmann, K., N. Yanaihara, S. Lande and H. Yajima: Studies on Polypeptides. XXIII. Synthesis and Biological Activity of a Hexadecapeptide Corresponding to the N-Terminal Sequence of the Corticotropins. J. Amer. Chem. Soc. 84, 4470 (1962).

    CAS  Google Scholar 

  84. Honzl, J. and J. Rudinger: Amino-Acids and Peptides. XXXIII. Nitrosyl Chloride and Butyl Nitrite as Reagents in Peptide Synthesis by the Azide Method; Suppression of Amide Formation. Collect. Czech. Chem. Comm. 26, 2333 (1961).

    CAS  Google Scholar 

  85. Hope, D. B., V. V. S. Murti and V. du Vigneaud: A Highly Potent Analogue of Oxytocin, Desamino-oxytocin. J. Biol. Chem. 237, 1563 (1962).

    CAS  Google Scholar 

  86. Huguenin, R. L. et R. A. Boissonnas: Synthèses de la Phé2-arginine-vaso-pressine et de la Phé2-arginine-vasotocine et nouvelles synth’s de l’arginine-vasopressine et de l’arginine-vasotocine. Helv. Chim. Acta 45, 1629 (1962).

    CAS  Google Scholar 

  87. Huguenin, R. L., E. Stürmer, R. A. Boissonnas and B. Berde: Desamino-arginine-vasopressin, an Analogue of Arginine-vasopressin with High Anti-diuretic Activity. Experientia 21, 68 (1965).

    CAS  Google Scholar 

  88. Jakubke, H.-D.: Die Verwendung aktivierter Ester zur Peptidsynthese. Z. Chem. 6, 52 (1966).

    CAS  Google Scholar 

  89. Jakubke, H.-D. und A. Voigt: Über aktivierte Ester. VII. Untersuchungen über die peptidchemische Verwendbarkeit von Acylaminosäure-chinolyl-(8)-estern. Chem. Ber. 99, 2419 (1966).

    CAS  Google Scholar 

  90. Jaquenoud, P.-A. et R. A. Boissonnas: Synthèse de la Dé-Pro7-oxytocine, de 1a Dé-Leu8-oxytocine et de 1a Dé-Gly9-oxytocine. Helv. Chim. Acta 45, 1462 (1962).

    CAS  Google Scholar 

  91. Jorpes, E.: Sekretin. Nordisk Med. 76, 965 (1966).

    CAS  Google Scholar 

  92. Kappeler, H., B. Riniker, W. Rittel, P. Desaulles, R. Maier, B. Schär and M. Staehelin: Synthesis and Biological Activity of Peptides Related to ACTH. Siehe Lit. 32, p.

    Google Scholar 

  93. Kasafírek, E., K. Jošt, J. Rudinger and F. Šorm: Amino Acids and Peptides. LIV. Synthesis of Further Extended-chain Analogues of Oxytocin. Collect. Czech. Chem. Comm. 30, 2600 (1965).

    Google Scholar 

  94. Kasafírek, E., B. Räbek, J. Rudinger and F. Šorm: Amino Acids and Peptides. LXVI. Synthesis of Ten Extended-chain Analogues of Lysine Vaso-pressin. Collect. Czech. Chem. Comm. 31, 4581 (1966).

    Google Scholar 

  95. Katsoyannis, P. G., D. T. Gish and V. du Vigneaud: Synthetic Studies on Arginine-vasopressin: Condensation of S-Benzyl-N-carbobenzoxy-L-cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparagine and its O-Tosyl Derivative with S-Benzyl-L-cysteinyl-L-prolyl-L-arginylglycinamide. J. Amer. Chem. Soc. 79 4516.

    CAS  Google Scholar 

  96. Kessler, W. und B. Iselin: Selektive Spaltung substituierter Phenylsulfenyl-Schutzgruppen bei Peptidsynthesen. Helv. Chim. Acta 49, 1330 (1966).

    CAS  Google Scholar 

  97. Khosla, M. G., R. R. Smeby and F. M. Bumpus: Solid-phase Peptide Synthesis of [L-Alanin3-L-isoleucine5]-angiotensin. II. Biochemistry 6, 754 (1967).

    CAS  Google Scholar 

  98. Kiryushkin, A. A., YU. A. Ovchinnikov, I. V. Kozhevnikova and M. M. Shemyakin: Synthesis of Peptides on a Polymeric Support in Solution. Siehe Lit. 32, p. 100.

    Google Scholar 

  99. Kisfaludy, L. und S. Dualszky: p-Chlorcarbobenzoxyaminosäuren und-Peptide, I. Acta Chim. Hungar. 24, 301 (1960).

    CAS  Google Scholar 

  100. Klieger, E. und E. Schröder: Synthese von Ser3-Ileu8-Oxytocin und Des-amino-Ser4Ileu8-Oxytocin (Desamino-Isotocin). Tetrahedron Letters 1965,2067.

    Google Scholar 

  101. Kondo, M., H. Aoyagi, T. Kato and N. Izumiya: Studies of Peptide Antibiotics. VI. Syntheses of Cyclic Penta-and Decapeptides with a Glycyl-L-ornithyl-L-leucyl-D-phenylalanylglycyl Sequence. Bull. Chem. Soc. Japan 39, 2234 (1966).

    CAS  Google Scholar 

  102. Kovacs, J., L. Kisfaludy and M. Q. Ceprini: On the Optical Purity of Peptide Active Esters Prepared by N,N’-Dicyclohexylcarbodiimide and 7“Complexes” of N,N’-Dicyclohexylcarbodiimide-Pentachlorophenol and N,N’-Dicyclohexyl-carbodiimide-Pentafluorophenol. J. Amer. Chem. Soc. 89, 183 (1967).

    CAS  Google Scholar 

  103. Lande, S. and A. B. Lerner: The Biochemistry of Melanotropic Agents. Pharmacol. Rev. 19, 1 (1967).

    CAS  Google Scholar 

  104. Law, H. D.: Polypeptides of Medicinal Interest. In: G. P. Ellis and G. B. West (ed.): Progress in Medicinal Chemistry, vol. 4, p. 86. London: Butterworths. 1965.

    Google Scholar 

  105. Lenard, J. and A. B. Robinson: Use of Hydrogen Fluoride in Merrifield Solid-Phase Peptide Synthesis. J. Amer. Chem. Soc. 89, 181 (1967).

    CAS  Google Scholar 

  106. Li, C. H., L. Barnafi, M. ChrÉtien and D. Chung: Isolation and Amino-acid Sequence of β-LPH from Sheep Pituitary Glands. Nature 208, 1093 (1965).

    CAS  Google Scholar 

  107. Li, C. H., J. Meienhofer, E. Schnabel, D. Chung, T.-B. Lo and J. Rama-chandran: Synthesis of a Biologically Active Nonadecapeptide Corresponding to the First Nineteen Amino Acid Residues of Adrenocorticotropins. J. Amer. Chem. Soc. 83, 4449 (1961).

    CAS  Google Scholar 

  108. Loffet, A.: Synthesis of a Pentapeptide by the Merrifield Method. Experientia 23, 406 (1967).

    CAS  Google Scholar 

  109. Losse, G. und G. Bachmann: Chemie der Depsipeptide. I. Z. Chem. 4, 204 (1964).

    CAS  Google Scholar 

  110. Losse, G. und G. Bachmann: Chemie der Depsipeptide. II. Z. Chem. 4, 241 (1964).

    CAS  Google Scholar 

  111. Lübke, K., E. Schröder, R. Schmiechen und H. Gibian: Über Peptidsynthesen, XXII. Synthese von Eledoisin und Glu5-Eledoisin. Liebigs Ann. Chem. 679, 195 (1964).

    Google Scholar 

  112. Lübke, K., G. Zöllner and E. Schröder: The Influence of Substitution or Omission of an Amino Group on the Hypotensive Activity of the C-Terminal Sequences of Eledoisin. In: E. G. Erdös, N. Back and F. Sicuteri (ed.): Hypo-tensive Peptides. Proc. Internat. Sympos. Florence 1965, p. 45. New York: Springer. 1966.

    Google Scholar 

  113. Makhlouf, G. M., J. P. A. Mcmanus and W. I. Card: Action of the Penta-peptide (ICI 50123) on Gastric Secretion in Man. Gastroenterology 51, 455 (1966).

    CAS  Google Scholar 

  114. Marshall, G. R. and R. B. Merrifield: Synthesis of Angiotensins by the Solid-Phase Method. Biochemistry 4, 2394 (1965).

    Google Scholar 

  115. Meienhofer, J. and V. du Vigneaud: Preparation of Lysine-vasopressin through a Cyrstalline Protected Nonapeptide Intermediate and Purification of the Hormone by Chromatography. J. Amer. Chem. Soc. 82, 2279 (1960).

    Google Scholar 

  116. Merrifield, R. B.: Solid Phase Peptide Synthesis. I. The Synthesis of a Tetra-peptide. J. Amer. Chem. Soc. 85, 2149 (1963).

    CAS  Google Scholar 

  117. Merrifield, R. B.: Solid-Phase Peptide Synthesis. III. An Improved Synthesis of Bradykinin. Biochemistry 3, 1385 (1964).

    CAS  Google Scholar 

  118. Merrifield, R. B.: Solid Phase Peptide Synthesis. IV. The Synthesis of Methionyl-lysyl-bradykinin. J. Organ. Chem. (USA) 29, 3100 (1964).

    CAS  Google Scholar 

  119. Merrifield, R. B. and A. Marglin: Progress in Solid Phase Peptide Synthesis. The Synthesis of Bovine Insulin. Siehe Lit. 32, p. 85.

    Google Scholar 

  120. Morley, J. S.: Syntheses of Human Gastrin (I) and the Biological Properties of Analogues. Siehe Lit. 32, p. 226.

    Google Scholar 

  121. Morley, J. S., H.J. Tracy and R. A. Gregory: Structure-Function Relationships in the Active C-Terminal Tetrapeptide Sequence of Gastrin. Nature 207, 1356 (1965).

    CAS  Google Scholar 

  122. Najjar, V. A. and R. B. Merrifield: Solid Phase Peptide Synthesis. VI. The Use of the O-Nitrophenylsulfenyl Group in the Synthesis of the Octadeca-peptide Bradykininylbradykinin. Biochemistry 5, 3765 (1966).

    CAS  Google Scholar 

  123. Nesvadba, H., H. Bachmayer und H. Michl: Über die Synthese eines im Gift von Bombina variegata vorkommenden Hexapeptid-diamids. Monatsh. Chem. 96, 1125 (1965).

    CAS  Google Scholar 

  124. Nicolaides, E. D. and H. A. De Wald: Studies on the Synthesis of Poly-peptides. Bradykinin. J. Organ. Chem. (USA) 26, 3872 (1961).

    CAS  Google Scholar 

  125. Ohno, M., T. Kato, S. Makisumi and N. Izumiya: Studies of Peptide Antibiotics. IV. The Synthesis of Tyrocidine A. Bull. Chem. Soc. Japan 39, 1738 (1966).

    CAS  Google Scholar 

  126. Okawa, K.: Studies on Serine Peptides. I. Optical Resolution of O-Benzyl-DL-serine and Synthesis of DL-Serine Peptides. Bull. Chem. Soc. Japan 29, 486 (1956).

    CAS  Google Scholar 

  127. Ovchinnikov, Yu. A., A. A. KiryushkiN and M. M. Shemyakin: Total Synthesis of Sporidesmolide III. Tetrahedron Letters 1965, 1111.

    Google Scholar 

  128. Ovchinnikov, Yu. A., A. A. Kiryushkin and M. M. Shemyakin: Complete Synthesis of Sporidesmolides III and IV. Zhurn. Obshchei Khimii (USSR) 36, 620 (1966).

    CAS  Google Scholar 

  129. Patchornik, A., A. Berger and E. Katchalski: Carbobenzoxy Derivatives of Histidine, Imidazole and Benzimidazole. J. Amer. Chem. Soc. 79, 6416 (1957).

    CAS  Google Scholar 

  130. Patchornik, A., M. Fridkin and E. Katchalski: Synthesis of Linear and Cyclic Peptides with the Aid of Insoluble Active Esters of Amino Acids and Peptides. Siehe Lit. 32, p. 91.

    Google Scholar 

  131. Paulay, Z. and S. Bajusz: A Novel Protection for the Guanidino Group of Arginine. Acta Chim. Hungar. 43, 147 (1965).

    CAS  Google Scholar 

  132. Phillips, J. G. and D. Bellamy: Adrenocortical Hormones. In: U. S. v. Euler and H. Heller (ed.), Comparative Endocrinology, vol. 1, p. 208. New York-London: Academic Press. 1963.

    Google Scholar 

  133. Photaki, I.: A New Synthesis of Oxytocin Using S-Acyl Cysteines as Intermediates. J. Amer. Chem. Soc. 88, 2292 (1966).

    CAS  Google Scholar 

Fortschritte d. Chem. org. Naturst. XXVI 8

  1. Plattner, Pl. A., K. Vogler, R. O. Studer, P. Quitt und W. Keller-Schierlein: Synthesen in der Depsipeptidreihe, 1. Mitt. Synthese von Ennia-tin B. Helv. Chim. Acta 46, 927 (1963).

    CAS  Google Scholar 

  2. Pless, J. und R. A. Boissonnas: Über die Geschwindigkeit der Aminolyse von verschiedenen neuen, aktivierten, N-geschützten α-Aminosäure-phenyl-estern, insbesondere 2,4,5-Trichlorphenylestern. Helv. Chim. Acta 46, 1609 (1963).

    Google Scholar 

  3. Pless, J., E. Stürmer, St. Guttmann und R. A. Boissonnas: Kallidin, Synthese und Eigenschaften. Helv. Chim. Acta 45, 394 (1962).

    CAS  Google Scholar 

  4. Poduška, K., V. Gut, H. Zimmermannová, J. Rudinger and F Šorm: Synthesis of Peptides Related to Trypsin Sequences. Acta Chim. Hungar. 44, 165 (1965).

    Google Scholar 

  5. Poduška, K., H. Maassen van den Brink-Zimmermannová, J. Rudinger and F. Šorm: Some Contributions to the Chemistry of the o-Nitrophenyl-sulphenyl-Protecting Group. Siehe Lit. 32, p. 38.

    Google Scholar 

  6. Quitt, P., R. O. Studer und K. Vogler: Synthesen in der Depsipeptid-Reihe. 2. Mitt. Synthese von Enniatin A. Helv. Chim. Acta 46, 1715 (1963).

    CAS  Google Scholar 

  7. Ramachandran, J., D. Chung and C. H. Li: Adrenocorticotropins. XXXIV. Aspects of Structure-Activity Relationships of the ACTH Molecule. Synthesis of a Heptadecapeptide Amide, an Octadecapeptide Amide, and a Nona-decapeptide Amide Possessing High Biological Activities. J. Amer. Chem. Soc. 87, 2696 (1965).

    CAS  Google Scholar 

  8. Ravdel, G. A., M. P. Filatova, L. A. Shchukina, T. S. Paskhina, M. S. Suro-vikina, S. S. Trapeznikova and T. P. Egorova: 6-Glycine–-8-phenyllactic Acid Bradykinin. Its Synthesis, Biological Activity, and Splitting by Kininase (Carboxypeptidase N). J. Med. Chem. 10 242 (1967).

    CAS  Google Scholar 

  9. Riniker, B. und R. Schwyzer: Die sterische Einheitlichkeit des synthetischen Val5-Hypertensin II-Asp1-β-amids. Helv. Chim. Acta 44, 658 (1961).

    CAS  Google Scholar 

  10. Rothe, M. und F. Eisenbeiss: Cyclische Peptide. XIV. Synthese eines Gramicidin S-Analogen, Cyclo-(Val-Lys(BOC)-Leu-Gly-Pro)2 Z. Naturforsch. 21 b, 814 (1966).

    Google Scholar 

  11. Rudinger, J. (ed.): Oxytocin, Vasopressin and their Structural Analogues. Proc. 2nd Internat. Pharmacol. Meeting, Prague 1963. New York: Macmillan (Pergamon), and Praha: Czechosl. Med. Press. 1964.

    Google Scholar 

  12. Rudinger, J., J. Honzl and M. Zaoral: Synthetic Studies in the Oxytocin Field. III. An Alternative Synthesis of Oxytocin. Collect. Czech. Chem. Comm. 21, 202 (1956).

    Google Scholar 

  13. Rudinger, J. and K. Jošt: A Biologically Active Analogue of Oxytocin not Containing a Disulfide Group. Experientia 20, 570 (1964).

    CAS  Google Scholar 

  14. Ruttenberg, M. A., T. P. King and L. C. Craig: The Chemistry of Tyrocidine. VI. The Amino Acid Sequence of Tyrocidine C. Biochemistry 4, 11 (1965).

    CAS  Google Scholar 

  15. Sakakibara, S. and N. Inukai: The Trifluoroacetate Method of Peptide Synthesis. II. An Improved Synthesis of Bradykinin. Bull. Chem. Soc. Japan 39, 1567 (1966).

    CAS  Google Scholar 

  16. Sakakibara, S., Y. Nobuhara, Y. Shimonishi and R. Kiyoi: A Synthesis of Oxytocin. Bull. Chem. Soc. Japan 38, 120 (1965).

    CAS  Google Scholar 

  17. Sakakibara, S., Y. Shimonishi, M. Okada and Y. Kishida: Removal of Protective Groups by Anhydrous Hydrogen Fluoride. Siehe Lit. 32, p. 44.

    Google Scholar 

  18. Sakakibara, S., M. Shin, M. Fujino, Y. Shimonishi, S. Inoue and N. Inukai: t-Amyloxycarbonyl as a New Protecting Group in Peptide Synthesis. I. The Synthesis and Properties of N-t-Amyloxycarbonylamino Acids and Related Compounds. Bull. Chem. Soc. Japan 38, 1522 (19

    CAS  Google Scholar 

  19. Sandrin, Ed. and R. A. Boissonnas: Synthesis of Eledoisin. Experientia 18, 59 (1962).

    CAS  Google Scholar 

  20. Sandrin, Ed. and R. A. Boissonnas: Synthèse d’analogues structuraux de l’élédoïsine. Helv. Chim. Acta 47, 1294 (1964).

    CAS  Google Scholar 

  21. Sarges, R. and B. Witkop: Gramicidin A. V. The Structure of Valine-and Isoleucine-gramicidin A. J. Amer. Chem. Soc. 87, 2011 (1965).

    CAS  Google Scholar 

  22. Sarges, R. and B. Witkop: Gramicidin. VII. The Structure of Valine-and Isoleucine-gramicidin B. J. Amer. Chem. Soc. 87, 2027 (1965).

    CAS  Google Scholar 

  23. Schnabel, E.: Verbesserte Synthese von tert.-Butyloxycarbonyl aminosäuren durch pH-Stat-Reaktion. Liebigs Ann. Chem. 702, 188 (1967).

    CAS  Google Scholar 

  24. Schröder, E.: Über Peptidsynthesen. Synthese von Methionyl-Lysyl-Brady-kinin, einem Kinin aus Rinderblut. Experientia 20, 39 (1964).

    Google Scholar 

  25. Schröder, E.: Synthese und biologische Aktivität bradykininwirksamer Undeca-, Dodeca-und Tridecapeptide. Experientia 21, 271 (1965).

    Google Scholar 

  26. Schröder, E.: Über Peptidsynthesen, XL. 5. Mitt. über Angiotensin-Analoga Synthese des all-D-Val5-Angiotensin II-Asp1-β amids. Liebigs Ann. Chem. 692, 241 (1966).

    Google Scholar 

  27. Schröder, E. and R. Hempel: Bradykinin, Kallidin, and their Synthetic Analogues. Experientia 20, 529 (1964).

    Google Scholar 

  28. Schröder, E. und K. Lübke: Peptolide. Experientia 19, 57 (1963).

    Google Scholar 

  29. Schröder, E. und K. Lübke: Über Peptidsynthesen. C-terminale Teilsequenzen des Eledoisins und eledoisinanaloger Verbindungen. Experientia 20, 19 (1964).

    Google Scholar 

  30. Schröder, E. und K. Lübke: The Peptides. Methods of Peptide Synthesis, vol. 1. New York-London: Academic Press. 1965.

    Google Scholar 

  31. Schröder, E. und K. Lübke: The Peptides. Synthesis, Occurrence, and Action of Biologically Active Peptides, vol. 2. New York-London: Academic Press. 1966.

    Google Scholar 

  32. Schröder, E., K. Lübke und R. Hempel: D-Aminosäurehaltige Analoga des Eledoisins. Experientia 21, 70 (1965).

    Google Scholar 

  33. Schröder, E. und S. Matthes: Reinigung synthetischer Peptide mit der trägerfreien präparativen Durchfluß-Elektrophorese. J. Chromatogr. 17, 189 (1965).

    Google Scholar 

  34. Schwartz, I. L. and L. M. Livingston: Cellular and Molecular Aspects of the Antidiuretic Action of Vasopressins and Related Peptides. Vitamins and Horm. 22, 261 (1964).

    CAS  Google Scholar 

  35. Schwarz, H. and K. Arakawa: The Use of P-Nitrobenzyl Esters in Peptide Synthesis. J. Amer. Chem. Soc. 81, 5691 (1959).

    CAS  Google Scholar 

  36. Schwarz, H. and F.M. Bumpus: Synthesis of an Optically Pure Tetrapeptide Contained in Angiotensin. J. Amer. Chem. Soc. 81, 890 (1959).

    CAS  Google Scholar 

  37. Schwyzer, R.: Recent Synthetic Developments in the Field of Polypeptide Hormones. In: H. Peeters (ed.), Protides of the Biological Fluids. Proc. 9th Colloq., Bruges 1961, p. 27. Amsterdam-New York: Elsevier. 1962.

    Google Scholar 

  38. Schwyzer, R., A. Costopanagiotis und P. Sieber: Zwei Synthesen des α-Melanotropins (α-MSH) mit Hilfe leicht entfernbarer Schutzgruppen. Helv. Chim. Acta 46, 870 (1963).

    CAS  Google Scholar 

  39. Schwyzer, R., B. Iselin, H. Kappeler, B. Riniker, W. Rittel und H. Zuber: Synthese hochwirksamer Dekapeptide mit der Aminosäuresequenz des Val5-Hypertensins I (L-Asparagyl-L-arginyl-L-valyl-L-tyrosyl-L-valyl-L-histidyl-L-prolyl-L-phenylalanyl-L-histidyl-L-leucin und L-Asparaginyl-L-arginyl-L-valyl-L-tyrosyl-L-valyl-L-histidyl-L-prolyl-L-phenylalanyl-L-histidyl-L-leucin). Helv. Chim. Acta 41, 1273 (1958).

    CAS  Google Scholar 

  40. Schwyzer, R., B. Iselin, H. Kappeler, B. Riniker, W. Rittel und H. Zuber: Die Synthese des β-Melanotropins (β-MSH) mit der Aminosäuresequenz des bovinen Hormons. Helv. Chim. Acta 46, 1975 (1963).

    CAS  Google Scholar 

  41. Schwyzer, R. und H. Kappeler: Synthese eines Tetracosapeptides mit hoher corticotroper Wirksamkeit: β1–24-Corticotropin. Helv. Chim. Acta 46, 1550 (1963).

    CAS  Google Scholar 

  42. Schwyzer, R., H. Kappeler, B. Iselin, W. Rittel und H. Zuber: Synthese und biologische Aktivität von geschützten Polypeptidsequenzen des β-Melano-phoren-stimulierenden Hormons (β-MSH) des Rindes. Helv. Chim. Acta 42, 1702 (1959).

    CAS  Google Scholar 

  43. Schwyzer, R. und P. Sieber: Die Synthese von Gramicidin S. Helv. Chim. Acta 40, 624 (1957).

    CAS  Google Scholar 

  44. Schwyzer, R. und P. Sieber: Verdoppelungsreaktionen beim Ringschluß von Peptiden. I. Synthese von Gramicidin S und von bis-homo-Gramicidin S aus den Pentapeptid-Einheiten. 7. Mitt. über homodet cyclische Polypeptide. Helv. Chim. Acta 41, 2186 (1958).

    Google Scholar 

  45. Schwyzer, R. und P. Sieber: Total Synthesis of Adrenocorticotropic Hormone. Nature 199, 172 (1963).

    CAS  Google Scholar 

  46. Schwyzer, R., P. Sieber und H. Kappeler: Zur Synthese von N-t-Butyl-oxycarbonyl-aminosäuren. Helv. Chim. Acta 42, 2622 (1959).

    CAS  Google Scholar 

  47. Sewing, K.-Fr.: Die Bedeutung von Gastrin in der Magensaftsekretion. Dtsch. med. Wschr. 91, 1506 (1966).

    CAS  Google Scholar 

  48. Sheehan, J. C. and G. P. Hess: A New Method of Forming Peptide Bonds. J. Amer. Chem. Soc. 77, 1067 (1955).

    CAS  Google Scholar 

  49. Shemyakin, M. M., N. A. Aldanova, E. I. Vinogradova and M. Yu. Feigina: The Structure and Total Synthesis of Valinomycin. Tetrahedron Letters 1963, 1921.

    Google Scholar 

  50. Shemyakin, M. M., Yu. A. Ovchinnikov, V. R. Antonov, A. A. Kiryushkin, V. T. Ivanov, V. I. Shchelokov and A. M. Shkrob: Total Synthesis of Serratamolide. I. Synthesis of O,O’-Diaccetylserratamolide. Tetrahedron Letters 1964, 47.

    Google Scholar 

  51. Shemyakin, M. M., Yu. A. Ovchinnikov, V. T. Ivanov and A. V. Evstratov: Topochemical Approach in Studies of the Structure-Activity Relation: Enantio-enniatin B. Nature 213, 412 (1967).

    CAS  Google Scholar 

  52. Shemyakin, M. M., Yu. A. Ovchinnikov, V. T. Ivanov and A. A. Kiryushkin: The Structure of Enniatins and Related Antibiotics. Tetrahedron 19, 581 (1963).

    CAS  Google Scholar 

  53. Shemyakin, M. M., Yu. A. Ovchinnikov, V. T. Ivanov, A. A. Kiryushkin and K. Kh. Khalilulina: Depsipeptides. XLII. Structure and Complete Synthesis of Sporidesmolides I and II. Zhurn. Obshchei Khimii (USSR) 35, 1399 (1965).

    CAS  Google Scholar 

  54. Shemyakin, M. M., Yu. A. Ovchinnikov, V. T. Ivanov, A. A. Kiryushkin, G. L. Zhdanov and I. D. Ryabova: The Structure-Antimicrobial Relation of Depsipeptides. Experientia 19, 566 (1963).

    CAS  Google Scholar 

  55. Shemyakin, M. M., Yu. A. Ovchinnikov, V. T. Ivanov and I. D. Ryabova: Topochemical Approach to the Structure-Activity Relation, Retroenantio-Gly5,10-Gramicidin S. Experientia 23, 326 (1967).

    CAS  Google Scholar 

  56. Shemyakin, M. M., Yu. A. Ovchinnikov, A. A. Kiryushkin and V. T. Ivanov: Studies in Depsipeptide Chemistry, 25. The Structure and Total Synthesis of Enniatins A and B. Izvest. Akad. Nauk. SSSR, Khim. Ser. 1965, 1623.

    Google Scholar 

  57. Shemyakin, M. M., Yu. A. Ovchinnikov, A. A. Kiryushkin and I. V. Ko-zhevnikova: Synthesis of Peptides in Solution on a Polymeric Support. I. Synthesis of Glycylglycyl-L-leucylglycine. Tetrahedron Letters 1965, 2323.

    Google Scholar 

  58. Shemyakin, M. M., L. A. Shchukina, E. I. Vinogradova, G. A. Ravdel and Yu. A. Ovchinnikov: Mutual Replaceability of Amide and Ester Groups in Biologically Active Peptides and Depsipeptides. Experientia 22, 535 (1966).

    CAS  Google Scholar 

  59. Shemyakin, M. M., E. I. Vinogradova, M. Yu. Feigina, N. A. Aldanova, N. F. Loginova, I. D. Ryabova and I. A. Pavlenko: The Structure-Antimicrobial Relation for Valinomycin Depsipeptides. Experientia 21, 548 (1965).

    CAS  Google Scholar 

  60. Shipolini, R., A. F. Bradbury, G. L. Callewaert and C. A. Vernon: The Structure of Apamin. Chem. Commun. 1967, 679.

    Google Scholar 

  61. Skeggs, L. T., Jr., K. E. Lentz, J. R. Kahn and N. P. Shumway: The Synthesis of a Tetradecapeptide Renin Substrate. J. Exp. Medicine 108, 283 (1958).

    CAS  Google Scholar 

  62. Stewart, J. M. and D. W. Woolley: Threonine Analogs of Bradykinin Designed as Antimetabolites. Biochemistry 3, 700 (1964).

    CAS  Google Scholar 

  63. Studer, R. O.: Vergleich von synthetischem und natürlichem Arginin-vaso-pressin. Helv. Chim. Acta 46, 421 (1963).

    CAS  Google Scholar 

  64. Studer, R. O., W. Lergier, P. Lanz, E. Böhni und K. Vogler: Synthesen in der Polymyxinreihe, 10. Mitt. Die Synthese von Colistin A (Polymyxin E1). Helv. Chim. Acta 48, 1371 (1965).

    CAS  Google Scholar 

  65. Studer, R. O., W. Lergier und K. Vogler: Synthesen in der Polymyxinreihe, 11. Mitt. Die Synthese von Circulin A. Helv. Chim. Acta 49, 974 (1966).

    CAS  Google Scholar 

  66. Studer, R. O., P. Quitt, E. Böhni und K. Vogler: Synthesen in der Depsi-peptid-Reihe, 4. Mitt. Struktur und mikrobiologische Aktivität in der Ennian-tin-Reihe. Monatsh. Chem. 96, 461 (1965).

    CAS  Google Scholar 

  67. Stürmer, E.: Plasmakinine. Schweiz, med. Wschr. 96, 1667 (1966).

    Google Scholar 

  68. Stürmer E. und A. Fanchamps: Eledoisin-Chemie, Pharmakologie, klinischexperimentelle und vorläufige therapeutische Erfahrungen. Dtsch. med. Wschr. 90, 1012 (1965).

    Google Scholar 

  69. Stürmer, E., R. L. Huguenin, R. A. Boissonnas and B. Berde: Deamino1-phenylalanine2-arginine8-vasopressin: A Peptide with Highly Selective Anti-diuretic Activity. Experientia 21, 583 (1965).

    Google Scholar 

  70. Suzuki, T., K. Hayashi, K. Fujikawa and K. Tsukamoto: Contribution to the Elucidation of the Structure of Polymyxin B1 J. Biochemistry (Tokyo) 54, 555 (1963).

    CAS  Google Scholar 

  71. Taschner, E., C. Wasielewski und J. F. Biernat: Neue Veresterungsmethoden in der Peptidchemie, IV. Darstellung von tert.-Butylestern N-acylier-ter Aminosäuren mit Hilfe von tert.-Butylacetat. Liebigs Ann. Chem. 646, 119 (1961).

    CAS  Google Scholar 

  72. Tesser, G. I. und R. Schwyzer: Synthese des 17,18-Diornithin-β-corti-cotropin-(1–24)-tetracosapeptides, eines biologisch aktiven Analogons des adrenocorticotropen Hormons. Helv. Chim. Acta 49, 1013 (1966).

    CAS  Google Scholar 

  73. Tsou, C.-L., Y.-C. Du and G.-J. Xü: The Reduction of Insulin and its Benzyl Derivatives by Sodium in Liquid Ammonia and the Regeneration of Activity from the Reduced Products. Sci. Sinica (Peking) 10, 332 (1961).

    CAS  Google Scholar 

  74. Velluz, L., G. Amiard, J. Bartos, B. Goffinet et R. Heymès: Accès à l’ocy-tocine de synthèse, à l’aide d’intermédiaires S,N-tritylés. Bull. soc. chim. France 1956, 1464.

    Google Scholar 

  75. Vogler, K. and P. Lanz: Synthesis of All-D-Isomers in the Bradykinin Series. In: E. G. Erdös, N. Back and F. Sicuteri (ed.), Hypotensive Peptides. Proc. Internat. Sympos. Florence 1965, p. 14. New York: Springer. 1966.

    Google Scholar 

  76. Vogler, K. and R. O. Studer: The Chemistry of the Polymyxin Antibiotics. Experientia 22, 345 (1966).

    CAS  Google Scholar 

  77. Vogler, K., R. O. Studer, P. Lanz, W. Lergier und E. Böhni: Synthesen in der Polymyxin-Reihe, 9. Mitt. Synthese von Polymyxin B1. Helv. Chim. Acta. 48, 1161 (1965).

    CAS  Google Scholar 

  78. Vogler, K., R. O. Studer, W. Lergier und P. Lanz: Synthese von All-d-Val5-Angiotensin II-Asp1-β-Amid. Helv. Chim. Acta 48, 1407 (1965).

    CAS  Google Scholar 

  79. Waki, M. and N. Izumiya: Cyclosemigramicidin S. J. Amer. Chem. Soc. 89, 1278 (1967).

    CAS  Google Scholar 

  80. Walter, R. and V. Du Vigneaud: 6-Hemi-L-selenocystine-oxytocin and 1-Deamino-6-hemi-L-selenocystine-oxytocin, Highly Potent Isologs of Oxytocin and 1-Deamino-oxytocin. J. Amer. Chem. Soc. 87 4192 (1965).

    CAS  Google Scholar 

  81. Walter, R. and V. Du Vigneaud: 1-Deamino-1,6-L-selenocystine-oxytocin, a Highly Potent Isolog of 1-Deamino-oxytocin. J. Amer. Chem. Soc. 88, 1331 (1966).

    CAS  Google Scholar 

  82. Weygand, F., D. Hoffmann und E. Wünsch: Peptidsynthesen mit Dicyclo-hexylcarbodiimid unter Zusatz von N-Hydroxysuccinimid. Z. Naturforsch. 21 b, 426 (1966).

    Google Scholar 

  83. Weygand, F. und K. Hunger: Acylierung von Aminosäuren mit p-Methoxy-benzyloxycarbonyl-azid. Chem. Ber. 95, 1 (1962).

    CAS  Google Scholar 

  84. Weygand, F. und U. Ragnarsson: Peptidsynthesen mit Dicyclohexylcarbodi-imid unter Zusatz von N-Hydroxysuccinimid. II. Peptidsynthesen an einem festen Träger. Z. Naturforsch. 21b, 1141 (1966).

    Google Scholar 

  85. Wiegershausen, B. und I. Paegelow: Die Rolle der Kinine im pathologischen Geschehen. Deutsche Gesundheitsw. 21, 2092 (1966).

    CAS  Google Scholar 

  86. Wood, J. L. and V. Du Vigneaud: Racemization of Benzyl-1-Cysteine, with a New Method of Preparing d-Cystine. J. Biol. Chem. 130, 109 (1939).

    CAS  Google Scholar 

  87. Wünsch, E., A. Fontana und F. Drees: Zur Entacylierung von N-(2-Nitro-phenyl)-sulfenyl peptiden bei Anwesenheit von Tryptophan in der Peptid-sequenz. Z. Naturforsch. 22 b, 607 (1967).

    Google Scholar 

  88. Wünsch, E., G. Fries und A. Zwick: Beiträge zur Peptidsynthese. V. Darstellung und peptidsynthetische Verwendung von O-Benzyl-L-tyrosin. Chem. Ber. 91, 542 (1958).

    Google Scholar 

  89. Wünsch, E. und G. Fürst: Racematspaltung von O-Benzyl-DL-serin. Z. phy-siol. Chem. 329, 109 (1962).

    Google Scholar 

  90. Yajima, H. and K. Kubo: Studies on Peptides. II. Synthesis and Physiological Properties of D-Histidyl-D-phenylalanyl-D-arginyl-D-tryptophylglycine, an Optical Antipode of an Active Fragment of α-Melanocyte-Stimulating Hormone. J. Amer. Chem. Soc. 87, 2039 (1965).

    CAS  Google Scholar 

  91. Yamashiro, D.: Partition Chromatography of Oxytocin on “Sephadex”. Nature 201, 76 (1964).

    CAS  Google Scholar 

  92. Yamashiro, D., D. Gillessen and V. Du Vigneaud: Oxytoceine and Deamino-oxytoceine: Biochemistry 5, 3711 (1966).

    CAS  Google Scholar 

  93. Young, J. D., E. Benjamini, J. M. Stewart and C. Y. Leung: Immuno-chemical Studies on Tobacco Mosaic Virus Protein. V. The Solid-Phase Synthesis of Peptides of an Antigenically Active Decapeptide of Tobacco Mosaic Virus Protein and the Reaction of these Peptides with Antibodies to the Whole Protein. Biochemistry 6, 1455 (1967).

    CAS  Google Scholar 

  94. Zahn, H., T. Okuda and Y. Shimonishi: Merrifield Synthesis of Human Insulin Chains and Their Alteration During the Sodium Treatment. Siehe Lit. 32, p. 108.

    Google Scholar 

  95. Zaoral, M., J. Kolc and F. Šorm: Amino Acids and Peptides. LXXI. Synthesis of 1-Deamino-8-D-γ-Aminobutyrine-Vasopressin, 1-Deamino-8-D-Lysirce-Vasopressin, and 1-Deamino-8-D-Arginine-Vasopressin. Collect. Czech. Chem. Comm. 32, 1250 (1967).

    CAS  Google Scholar 

  96. Zervas, L. (ed.): Peptides. Proc. 6th Europ. Sympos., Athens 1963. Oxford, London, Edinburgh, New York, Paris, Frankfurt: Pergamon Press. 1965.

    Google Scholar 

  97. Zervas, L., D. Borovas and E. Gazis: New Methods in Peptide Synthesis. I. Tritylsulfenyl and o-Nitrophenylsulfenyl Groups as N-Protecting Groups. J. Amer. Chem. Soc. 85, 3660 (1963).

    CAS  Google Scholar 

  98. Zhuze, A. L., K. Jošt, E. Kasafírek and J. Rudinger: Amino Acids and Peptides. XLV. Analogues of Oxytocin with O-Ethyltyrosine, p-Methylphenyl-alanine, and p-Ethylphenylalanine Replacing Tyrosine. Collect. Czech. Chem. Comm. 29, 2648 (1964).

    CAS  Google Scholar 

  99. Zuber, H.: Die Verwendung enzymatischer Reaktionen für die Reinheits-prüfung und Strukturaufklärung von Peptiden und Proteinen. Chimia 14, 405 (1960).

    Google Scholar 

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Schröder, E., Lübke, K. (1968). Synthese von Peptiden und Peptidwirkstoffen. In: Zechmeister, L. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 26. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7134-9_2

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