Abstract
In the synthesis and isolation of naturally occurring macromolecules, especially polypeptides, the two major methods of purification employed in organic synthesis, namely, recrystallization and fractional distillation, are usually not applicable. Only in the so-called lower region of smaller peptides or in a very few special cases is it possible to obtain pure materials by crystallization; in the so-called upper region of larger peptides, crystallization is successful only if preceded by other methods of purification. The present situation of research into the purification of polypeptide hormones can be comprehensively considered using as examples the total syntheses of the hormones glucagon, secretin, and [leucine-15]-human gastrin I, an analogue of the natural product.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Alakhov, Yu. B., Kiryushkin, A. A., Lipkin, V. M., and Milne, G. W. A., 1970, Butylation of the tryptophan indole ring: A side reaction during the removal of t-butyloxycarbonyl and t-butyl protecting groups in peptide synthesis, Chem. Commun. 1970:406.
Assan, R. Drouet, J.. Rosselin. G., Wünsch, E., and Schröder, E., 1969, Étude radio-immunologique de glucagons naturel et synthétique et de peptides synthétiques apparentés, Path. Biol. 17:757.
Beaven, G. H.. and Holiday, E. R. 1952, Ultraviolet absorption spectra of proteins and amino acids, Advan. Protein Chem. 7:319.
Bencze, W. L.. and Schmid. K.. 1957. Determination of tyrosine and tryptophan in proteins, Anal. Chem. 29:1193.
Feurle, G., Ketterer. H. Becker, H. D. and Creutzfeldt, W., 1972, Circadian serum gastrin concentration in control persons and in patients with ulcer disease, Gastroenterologie 7:177.
Gregory, R. A., and Tracy, H. J., 1964b, Constitution and properties of two gastrins extracted from hog antral mucosa, Gut 5:103.
Gregory, R. A.. Hardy. P. M., Jones, D. S., Kenner, G. W., and Sheppard, R. C., 1964, The antral hormone gastrin. Nature 204:931.
Gregory, R. A.. Tracy, H. J.. and Grossman, M. I. 1966, Human gastrin: Isolation, structure and synthesis. Nature 209:583.
Hannig, K., 1964. Eine Neuentwicklung der trägerfreien kontinuierlichen Elektrophorese, Hoppe-Seyler’s Z. Physiol. Chem. 338:211.
Jaeger, E., Deffner, M.. Deimer. K.-H., Scharf, R., and Wunsch, E., 1971, Zur Reindarstellung der synthetischen Peptidwirkstoffe Sekretin, [15-Leucin]-Human-Gastrin I und Glucagon, in “Proceedings of the Eleventh European Peptide Symposium, Wien, 1971,” North Holland Publ. Co. Amsterdam (1973), p. 237.
Jorpes, J. E., and Mutt, V. 1959, Secretin, pancreozymin, and cholecystokinin: Their preparation and properties, Gastroenterologie 36:377.
Jorpes, J. E., and Mutt. V. 1961. On the biological activity and amino acid composition of secretin, Acta Chem. Scand. 15:1790.
Kenner, G. W., Mendive. J. J.. and Sheppard, R. C., 1968, Peptides. Part XXVI. Analogues of gastrin containing leucine in place of methionine, J. Chem. Soc. (C) 1968:761.
Konz, B. Holle. F.. Wünsch, E.. Kissler, K., and Leimer, E., 1971, Magensekretion nach Stimulation mit 15-Leucin]-Human-Gastrin 1, Gastroenterologie 9:413.
Lehnert, P.. Stahlheber, H., Forell. M. M., Dost, F. H., Fritz, H., Hutzel, M., and Werle, E., 1969, Bestimmung der Halbwertzeit von Sekretin, Klin. Wschr. 47:1200.
Lehnert, P. Stahlheber, H. Roder. O., Zoelch, M., Forell, M. M., Wunsch, E., Jaeger, E., and Martens, H. L.. 1973. Bestimmung der biologischen Aktivität von synthetischem Sekretin. Klin. Wschr. 51:44.
Markussen. J.. 1972. Private communication.
Morley. J. S., and Smith. J. M., 1968, Variations of the methionyl position in the C-terminal tetrapeptide amide sequence of the gastrins, J. Chem. Soc. (C) 1968:726.
Morley, J. S.. Tracy, H. J.. and Gregory, R. A., 1965, Structure function relationships in the active C-terminal tetrapeptide sequence of gastrin, Nature 207:1356.
Mutt, V., Magnusson, S.. Jorpes, J. E.. and Dahl, E., 1966, Structure of porcine secretin. I. Degradation with trypsin and thrombin. Sequence of the tryptic peptides. The C-terminal residue, Biochemistry 4:2358.
Valverde. I.. Rigopoulou. D.. Marco. J.. Faloona, G. R. and Unger, R. H., 1970, Molecular size of extractable glucagon and glucagon-like immunoreactivity (GLI) in plasma, Diabetes 19:624
Weinges, K. F., 1968, Untersuchungen der biologischen Aktivität und immunologischen Reaktionsfähigkeit von synthetischem Glucagon. in “Fourteenth Symp. Deutsch. Ges. Endokrinol.,” p. 219. Springer-Verlag, Berlin, Heidelberg, New York.
Weinges, K. F., Wünsch, E., Biro, G.. Kettl, H., and Mitzuno, M., 1969, The immunological reactivity and biological activity of synthetic glucagon, Diabetologia 5:97.
Wendlberger, G., Högel, A., Thamm, P., Spangenberg, R., and Wünsch, E., 1971, Eine neue Totalsynthese des Sekretins. in Proceedings of the Eleventh European Peptide Symposium, Wien, 1971, North Holland Publ. Co. Amsterdam (1973), p. 96.
Wünsch, E., 1967, Die Totalsynthese des Pankreas-Hormons Glucagon, Z. Naturforsch. 226:1269.
Wünsch, E., 1968, Die Biochemie der Polypeptid-Naturstoffe: Totalsynthese des biologisch-wirksamen Glucagons. in “Fourteenth Symp. Deutsch. Ges. Endokrinol.,” p. 206, Springer-Verlag, Berlin, Heidelberg. New York.
Wünsch, E., and Deimer. K.-H.. I972a, Zur Synthese des [15-Leucin]-Human-Gastrins I, II. Mitteilung. Erstellung der Gesamtsequenz, Hoppe-Seyler’s Z. Physiol. Chem. 353:1255.
Wünsch, E.. and Deimer. K.-H.. 1972, Zur Synthese des [15-Leucin]-Human-Gastrins I, I. Mitteilung. Erstellung der Teilsequenzen 1–5, 6–13 und 14–17, Hoppe-Seyler’s Z. Physiol. Chem. 353:1246.
Wünsch, E.. and Drees, F.. 1967, Zur Synthese des Glucagons. XIII. Darstellung der Sequenz 22–29 (neuer Weg), Chem. Ber. 100:816.
Wünsch, E.. and Thamm, P. 1971, Zur Synthese des Sekretins. III. Darstellung der Sequenz 7–11, Chem. Ber. 104:2454.
Wünsch, E., and Wendlberger. G.. 1968a, Zur Synthese des Glucagons. XVIII. Darstellung der Gesamtsequenz, Chem. Ber. 101:3659.
Wünsch, E.. and Wendlberger. G., 1968b. Zur Synthese des Glucagons. XVII. Darstellung der Sequenz 7–29, Chem. Ber. 101:341.
Wünsch, E., Drees, F., and Jentsch, J., 1965. Zur Synthese des Glucagons. VII. Darstellung der Sequenz 24–29, Chem. Ber 98:803.
Wünsch, E., Zwick. A., and Fontana. A.. 1968a, Zur Synthese des Glucagons. XV. Darstellung der Sequenzen 7–15 und 7 23. Chem. Ber. 101:326.
Wünsch, E.. Zwick, A., and Jaeger, E.. 19686, Zur Synthese des Glucagons. XVI. Darstellung der Sequenz 1–6, (hem. Ber. 101:336.
Wunsch, E.. Jaeger, E.. and Scharf. R.. 1968e. Zur Synthese des Glucagons. XIX. Reindarstellung des synthetischen Glucagons. Chem. Ber. 101:3664.
Wunsch, E., Wendlberger. G., Jaeger, E., and Scharf, R. 1968d, Zur Totalsynthese des biologisch-aktiven Pankreas-Hormons Glucagon, in “Peptides-1968: Proceedings of the Ninth European Peptide Symposium.” p. 229, North-Holland, Amsterdam.
Wünsch, E., Konz, B. and Holle. F., 197la. Gastric secretion in man after stimulation with a new human-gastrin 1. in “Proceedings of the International Union of Physiological Sciences.- Vol. IX, p. 610, Munich.
Wunsch, E., Wendlberger. G., and Högel, A., 19716, Zur Synthese des Sekretins. I. Darstellung der Sequenz 18–27. Chern Ber. 104:2430.
Wünsch, E.. Wendlberger. G.. and Thamm, P., 1971e, Zur Synthese des Sekretins. II. Darstellung der Sequenz 12–27. Chem. Ber. 104:2445.
Wünsch, E., Wendlberger. G.. and Spangenberg, R. 1971d, Zur Synthese des Sekretins. IV. Darstellung der Sequenz I 6. Chem. Ber. 104:3854.
Wünsch, E., Jaeger, E., Deffner, M.. and Scharf, R., 1972a, Zur Synthese des [15-Leucin]?Human-Gastrins I. III. Mitteilung. Reindarstellung des synthetischen Hormons, Hoppe?Seyler’s Z. Physiol. Chem. 353: 1 716.
Wünsch, E., Jaeger, E.. Deffner. M.. Scharf, R. and Lehnert, P., 1972, Zur Synthese des Sekretins. VI. Reindarstellung des synthetischen Sekretins, Chem. Ber. 105:2515.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1973 Plenum Press, New York
About this chapter
Cite this chapter
Wünsch, E. (1973). Synthesis of Pure Polypeptide Hormones with Full Biological Activity. In: Katsoyannis, P.G. (eds) The Chemistry of Polypeptides. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4571-8_13
Download citation
DOI: https://doi.org/10.1007/978-1-4613-4571-8_13
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-4573-2
Online ISBN: 978-1-4613-4571-8
eBook Packages: Springer Book Archive