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
Acher, R., J. Chauvet, M. T. Chauvet et D. Crepy: Phylogénie des peptides hormonaux neurohypophysaires. Bull. soc. chim. biol. (Paris) 47, 2279 (1965).
Albertson, N. F.: Synthesis of Peptides with Mixed Anhydrides. Organ. React. 12, 157 (1962).
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).
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).
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).
Anderson, G. W. and A. C. McGregor: t-Butyloxycarbonylamino Acids and Their Use in Peptide Synthesis. J. Amer. Chem. Soc. 79, 6180 (1957).
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).
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).
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).
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).
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).
Arakawa, K. and F. M. Bumpus: An Improved Synthesis of Isoleucine5 Angiotensin Octapeptide. J. Amer. Chem. Soc. 83, 728 (1961).
Arakawa, K., M. Nakatani and M. Nakamura: Purification of Human Angiotensin. Nature 214, 278 (1967).
Bajusz, S.: A Novel Synthesis of Eledoisin. Acta Chim. Hungar. 42, 383 (1964).
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.
Bajusz, S. und K. Medzihradszky: Synthesis and Biological Activity of Corticotropin Fragments. Siehe Lit. 32, p. 209.
Bajusz, S., K. Medzihradszky, Z. Paulay und Zs. Láng: Totalsynthese des menschlichen Corticotropins (αh-ACTH). Acta Chim. Hungar. 52, 335 (1967)
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).
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.
Berger, A., J. Noguchi and E. Katchalski: Poly-L-cysteine. J. Amer. Chem. Soc. 78, 4483 (1956).
Bergmann, M. und L. Zervas: Über ein allgemeines Verfahren der Peptid-synthese. Ber. dtsch. chem. Ges. 65, 1192 (1932).
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.
Bernardi, L., G. Bosisio, R. de Castiglione and O. Goffredo: Synthesis of Phyllokinin, a Natural Bradykinin Analogue. Experientia 22, 425 (1966).
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).
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).
Bernardi, L., G. Bosisio, O. Goffredo and R. de Castiglione: Synthesis of Physalaemin. Experientia 20, 490 (1964).
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).
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).
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).
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).
Beyerman, H. C, J. S. Bontekoe and A. C. Koch: A Synthesis of Oxytocin. Rec. trav. chim. Pays-Bas 78, 935 (1959).
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.
Bodanszky, M. and V. du Vigneaud: An Improved Synthesis of Oxytocin. J. Amer. Chem. Soc. 81, 2504 (1
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
Bodanszky, M., J. Meienhofer and V. du Vigneaud: Synthesis of Lysine-vasopressin by the Nitrophenyl Ester Method. J. Amer. Chem. Soc. 82, 3195 (1960).
Bodanszky, M. and M. A. Ondetti: Peptide Synthesis. New York: J. Wiley and Sons. 1966.
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).
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.
Bodanszky, M. and D. Perlman: Are Peptide Antibiotics Small Proteins? Nature 204, 840 (1964).
Bodanszky, M. and J. T. Sheehan: Active Esters and Resins in Peptide Synthesis. Chem. and Ind. 1964, 1423.
Bodanszky, M., M. Szelke, E. TömörkÉny and E. Weisz: Peptide Synthesis by Aminolysis of Active Esters. Chem. and Ind. 1955, 1517.
Boissonnas, R. A.: Selectively Removable Amino Protective Groups Used in the Synthesis of Peptides. Adv. Organ. Chem. 3, 159 (1963).
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).
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).
Boissonnas, R. A., St. Guttmann, P.-A. Jaquenoud et J.-P. Waller: Une nouvelle synthèse de l’oxytocine. Helv. Chim. Acta 38, 1491 (1955).
Boissonnas, R. A., St. Guttmann, J.-P. Waller and P.-A. Jaquenoud: Synthesis of a Polypeptide with ACTH-like Structure. Experientia 12, 446 (1956).
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).
Bruckner, V. and K. Medzihradszky (ed.): Proc. 7th Europ. Peptide Sympos., Budapest 1964; Acta Chim. Hungar. 44 (1965).
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).
Carpenter, F. H. and D. T. Gish: The Application of P-Nitrobenzyl Chloro-formate to Peptide Synthesis. J. Amer. Chem. Soc. 74, 3818 (1952).
Chillemi, F.: Sintesi della fisalemina, un endecapeptide biologicamente attivo del „Physalaemus fuscumaculatus“. Gazz. chim. ital. 95, 402 (1965).
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).
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).
Determann, H.: Gelchromatographie. Gelfiltration, Gelpermeation, Molekülsiebe. Berlin, Heidelberg, New York: Springer-Verl. 1967.
Doepfner, W.: Biological Characterization of a New and Highly Potent Synthetic Analogue of Corticotrophin. Experientia 22, 527 (1966).
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).
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).
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).
Fontana, A., F. Marchiori, L. Moroder and E. Scoffone: New Removal Conditions of Sulfenyl Groups in Peptide Synthesis. Tetrahedron Letters 1966, 2985.
Fridkin, M., A. Patchornik and E. Katchalski: A Synthesis of Cyclic Peptides Utilizing High Molecular Weight Carriers. J. Amer. Chem. Soc. 87, 4646 (1965).
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).
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).
Greenstein, J. P. and M. Winitz: Chemistry of the Amino Acids. New York-London: J. Wiley and Sons. 1961.
Gregory, H., P. M. Hardy, D. S. Jones, G. W. Kenner and R. C. Shep-pard: The Antral Hormone Gastrin. Nature 204, 931 (1964).
Gross, F.: Angiotensin. Arch. exp. Pathol. Pharmakol. 245, 196 (1963).
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.
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).
Guttmann, St. et R. A. Boissonnas: Synthèse de l’α-mélanotropine (α-MSH) de Porc. Helv. Chim. Acta 42, 1257 (1959).
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).
Guttmann, St. and J. Pless: On the Protection of the Guanidino Group of Arginine. Acta Chim. Hungar. 44, 23 (1965).
Guttmann, St., J. Pless and R. A. Boissonnas: Synthesis of Peptides Related to ACTH. Acta Chim. Hungar. 44, 141 (1965).
— Synthesis of a Highly Active Peptide Related to Corticotropin. Siehe Lit. 32, p. 221.
Habermann, E.: Strukturaufklärung kininliefernder Peptide aus Rinderserum-Kininogen. Arch. exp. Pathol. Pharmakol. 253, 474 (1966).
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).
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.
Haux, P., H. Sawerthal und E. Habermann: Sequenzanalyse des Bienengift-Neurotoxin (Apamin) aus seinen tryptischen und chymotryptischen Spaltstücken. Z. physiol. Chem. 348, 737 (1967).
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.
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.
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.
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).
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).
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).
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).
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).
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).
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).
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).
Jakubke, H.-D.: Die Verwendung aktivierter Ester zur Peptidsynthese. Z. Chem. 6, 52 (1966).
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).
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).
Jorpes, E.: Sekretin. Nordisk Med. 76, 965 (1966).
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.
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).
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).
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.
Kessler, W. und B. Iselin: Selektive Spaltung substituierter Phenylsulfenyl-Schutzgruppen bei Peptidsynthesen. Helv. Chim. Acta 49, 1330 (1966).
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).
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.
Kisfaludy, L. und S. Dualszky: p-Chlorcarbobenzoxyaminosäuren und-Peptide, I. Acta Chim. Hungar. 24, 301 (1960).
Klieger, E. und E. Schröder: Synthese von Ser3-Ileu8-Oxytocin und Des-amino-Ser4Ileu8-Oxytocin (Desamino-Isotocin). Tetrahedron Letters 1965,2067.
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).
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).
Lande, S. and A. B. Lerner: The Biochemistry of Melanotropic Agents. Pharmacol. Rev. 19, 1 (1967).
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.
Lenard, J. and A. B. Robinson: Use of Hydrogen Fluoride in Merrifield Solid-Phase Peptide Synthesis. J. Amer. Chem. Soc. 89, 181 (1967).
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).
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).
Loffet, A.: Synthesis of a Pentapeptide by the Merrifield Method. Experientia 23, 406 (1967).
Losse, G. und G. Bachmann: Chemie der Depsipeptide. I. Z. Chem. 4, 204 (1964).
Losse, G. und G. Bachmann: Chemie der Depsipeptide. II. Z. Chem. 4, 241 (1964).
Lübke, K., E. Schröder, R. Schmiechen und H. Gibian: Über Peptidsynthesen, XXII. Synthese von Eledoisin und Glu5-Eledoisin. Liebigs Ann. Chem. 679, 195 (1964).
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.
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).
Marshall, G. R. and R. B. Merrifield: Synthesis of Angiotensins by the Solid-Phase Method. Biochemistry 4, 2394 (1965).
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).
Merrifield, R. B.: Solid Phase Peptide Synthesis. I. The Synthesis of a Tetra-peptide. J. Amer. Chem. Soc. 85, 2149 (1963).
Merrifield, R. B.: Solid-Phase Peptide Synthesis. III. An Improved Synthesis of Bradykinin. Biochemistry 3, 1385 (1964).
Merrifield, R. B.: Solid Phase Peptide Synthesis. IV. The Synthesis of Methionyl-lysyl-bradykinin. J. Organ. Chem. (USA) 29, 3100 (1964).
Merrifield, R. B. and A. Marglin: Progress in Solid Phase Peptide Synthesis. The Synthesis of Bovine Insulin. Siehe Lit. 32, p. 85.
Morley, J. S.: Syntheses of Human Gastrin (I) and the Biological Properties of Analogues. Siehe Lit. 32, p. 226.
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).
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).
Nesvadba, H., H. Bachmayer und H. Michl: Über die Synthese eines im Gift von Bombina variegata vorkommenden Hexapeptid-diamids. Monatsh. Chem. 96, 1125 (1965).
Nicolaides, E. D. and H. A. De Wald: Studies on the Synthesis of Poly-peptides. Bradykinin. J. Organ. Chem. (USA) 26, 3872 (1961).
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).
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).
Ovchinnikov, Yu. A., A. A. KiryushkiN and M. M. Shemyakin: Total Synthesis of Sporidesmolide III. Tetrahedron Letters 1965, 1111.
Ovchinnikov, Yu. A., A. A. Kiryushkin and M. M. Shemyakin: Complete Synthesis of Sporidesmolides III and IV. Zhurn. Obshchei Khimii (USSR) 36, 620 (1966).
Patchornik, A., A. Berger and E. Katchalski: Carbobenzoxy Derivatives of Histidine, Imidazole and Benzimidazole. J. Amer. Chem. Soc. 79, 6416 (1957).
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.
Paulay, Z. and S. Bajusz: A Novel Protection for the Guanidino Group of Arginine. Acta Chim. Hungar. 43, 147 (1965).
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.
Photaki, I.: A New Synthesis of Oxytocin Using S-Acyl Cysteines as Intermediates. J. Amer. Chem. Soc. 88, 2292 (1966).
Fortschritte d. Chem. org. Naturst. XXVI 8
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).
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).
Pless, J., E. Stürmer, St. Guttmann und R. A. Boissonnas: Kallidin, Synthese und Eigenschaften. Helv. Chim. Acta 45, 394 (1962).
Poduška, K., V. Gut, H. Zimmermannová, J. Rudinger and F Šorm: Synthesis of Peptides Related to Trypsin Sequences. Acta Chim. Hungar. 44, 165 (1965).
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.
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).
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).
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).
Riniker, B. und R. Schwyzer: Die sterische Einheitlichkeit des synthetischen Val5-Hypertensin II-Asp1-β-amids. Helv. Chim. Acta 44, 658 (1961).
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).
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.
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).
Rudinger, J. and K. Jošt: A Biologically Active Analogue of Oxytocin not Containing a Disulfide Group. Experientia 20, 570 (1964).
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).
Sakakibara, S. and N. Inukai: The Trifluoroacetate Method of Peptide Synthesis. II. An Improved Synthesis of Bradykinin. Bull. Chem. Soc. Japan 39, 1567 (1966).
Sakakibara, S., Y. Nobuhara, Y. Shimonishi and R. Kiyoi: A Synthesis of Oxytocin. Bull. Chem. Soc. Japan 38, 120 (1965).
Sakakibara, S., Y. Shimonishi, M. Okada and Y. Kishida: Removal of Protective Groups by Anhydrous Hydrogen Fluoride. Siehe Lit. 32, p. 44.
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
Sandrin, Ed. and R. A. Boissonnas: Synthesis of Eledoisin. Experientia 18, 59 (1962).
Sandrin, Ed. and R. A. Boissonnas: Synthèse d’analogues structuraux de l’élédoïsine. Helv. Chim. Acta 47, 1294 (1964).
Sarges, R. and B. Witkop: Gramicidin A. V. The Structure of Valine-and Isoleucine-gramicidin A. J. Amer. Chem. Soc. 87, 2011 (1965).
Sarges, R. and B. Witkop: Gramicidin. VII. The Structure of Valine-and Isoleucine-gramicidin B. J. Amer. Chem. Soc. 87, 2027 (1965).
Schnabel, E.: Verbesserte Synthese von tert.-Butyloxycarbonyl aminosäuren durch pH-Stat-Reaktion. Liebigs Ann. Chem. 702, 188 (1967).
Schröder, E.: Über Peptidsynthesen. Synthese von Methionyl-Lysyl-Brady-kinin, einem Kinin aus Rinderblut. Experientia 20, 39 (1964).
Schröder, E.: Synthese und biologische Aktivität bradykininwirksamer Undeca-, Dodeca-und Tridecapeptide. Experientia 21, 271 (1965).
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).
Schröder, E. and R. Hempel: Bradykinin, Kallidin, and their Synthetic Analogues. Experientia 20, 529 (1964).
Schröder, E. und K. Lübke: Peptolide. Experientia 19, 57 (1963).
Schröder, E. und K. Lübke: Über Peptidsynthesen. C-terminale Teilsequenzen des Eledoisins und eledoisinanaloger Verbindungen. Experientia 20, 19 (1964).
Schröder, E. und K. Lübke: The Peptides. Methods of Peptide Synthesis, vol. 1. New York-London: Academic Press. 1965.
Schröder, E. und K. Lübke: The Peptides. Synthesis, Occurrence, and Action of Biologically Active Peptides, vol. 2. New York-London: Academic Press. 1966.
Schröder, E., K. Lübke und R. Hempel: D-Aminosäurehaltige Analoga des Eledoisins. Experientia 21, 70 (1965).
Schröder, E. und S. Matthes: Reinigung synthetischer Peptide mit der trägerfreien präparativen Durchfluß-Elektrophorese. J. Chromatogr. 17, 189 (1965).
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).
Schwarz, H. and K. Arakawa: The Use of P-Nitrobenzyl Esters in Peptide Synthesis. J. Amer. Chem. Soc. 81, 5691 (1959).
Schwarz, H. and F.M. Bumpus: Synthesis of an Optically Pure Tetrapeptide Contained in Angiotensin. J. Amer. Chem. Soc. 81, 890 (1959).
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.
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).
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).
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).
Schwyzer, R. und H. Kappeler: Synthese eines Tetracosapeptides mit hoher corticotroper Wirksamkeit: β1–24-Corticotropin. Helv. Chim. Acta 46, 1550 (1963).
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).
Schwyzer, R. und P. Sieber: Die Synthese von Gramicidin S. Helv. Chim. Acta 40, 624 (1957).
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).
Schwyzer, R. und P. Sieber: Total Synthesis of Adrenocorticotropic Hormone. Nature 199, 172 (1963).
Schwyzer, R., P. Sieber und H. Kappeler: Zur Synthese von N-t-Butyl-oxycarbonyl-aminosäuren. Helv. Chim. Acta 42, 2622 (1959).
Sewing, K.-Fr.: Die Bedeutung von Gastrin in der Magensaftsekretion. Dtsch. med. Wschr. 91, 1506 (1966).
Sheehan, J. C. and G. P. Hess: A New Method of Forming Peptide Bonds. J. Amer. Chem. Soc. 77, 1067 (1955).
Shemyakin, M. M., N. A. Aldanova, E. I. Vinogradova and M. Yu. Feigina: The Structure and Total Synthesis of Valinomycin. Tetrahedron Letters 1963, 1921.
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.
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).
Shemyakin, M. M., Yu. A. Ovchinnikov, V. T. Ivanov and A. A. Kiryushkin: The Structure of Enniatins and Related Antibiotics. Tetrahedron 19, 581 (1963).
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).
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).
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).
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.
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.
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).
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).
Shipolini, R., A. F. Bradbury, G. L. Callewaert and C. A. Vernon: The Structure of Apamin. Chem. Commun. 1967, 679.
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).
Stewart, J. M. and D. W. Woolley: Threonine Analogs of Bradykinin Designed as Antimetabolites. Biochemistry 3, 700 (1964).
Studer, R. O.: Vergleich von synthetischem und natürlichem Arginin-vaso-pressin. Helv. Chim. Acta 46, 421 (1963).
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).
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).
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).
Stürmer, E.: Plasmakinine. Schweiz, med. Wschr. 96, 1667 (1966).
Stürmer E. und A. Fanchamps: Eledoisin-Chemie, Pharmakologie, klinischexperimentelle und vorläufige therapeutische Erfahrungen. Dtsch. med. Wschr. 90, 1012 (1965).
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).
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).
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).
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).
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).
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.
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.
Vogler, K. and R. O. Studer: The Chemistry of the Polymyxin Antibiotics. Experientia 22, 345 (1966).
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).
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).
Waki, M. and N. Izumiya: Cyclosemigramicidin S. J. Amer. Chem. Soc. 89, 1278 (1967).
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).
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).
Weygand, F., D. Hoffmann und E. Wünsch: Peptidsynthesen mit Dicyclo-hexylcarbodiimid unter Zusatz von N-Hydroxysuccinimid. Z. Naturforsch. 21 b, 426 (1966).
Weygand, F. und K. Hunger: Acylierung von Aminosäuren mit p-Methoxy-benzyloxycarbonyl-azid. Chem. Ber. 95, 1 (1962).
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).
Wiegershausen, B. und I. Paegelow: Die Rolle der Kinine im pathologischen Geschehen. Deutsche Gesundheitsw. 21, 2092 (1966).
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).
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).
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).
Wünsch, E. und G. Fürst: Racematspaltung von O-Benzyl-DL-serin. Z. phy-siol. Chem. 329, 109 (1962).
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).
Yamashiro, D.: Partition Chromatography of Oxytocin on “Sephadex”. Nature 201, 76 (1964).
Yamashiro, D., D. Gillessen and V. Du Vigneaud: Oxytoceine and Deamino-oxytoceine: Biochemistry 5, 3711 (1966).
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).
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.
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).
Zervas, L. (ed.): Peptides. Proc. 6th Europ. Sympos., Athens 1963. Oxford, London, Edinburgh, New York, Paris, Frankfurt: Pergamon Press. 1965.
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).
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).
Zuber, H.: Die Verwendung enzymatischer Reaktionen für die Reinheits-prüfung und Strukturaufklärung von Peptiden und Proteinen. Chimia 14, 405 (1960).
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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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