Abstract
The chemical synthesis of bradykinin has a remarkable history, for this peptide hormone was successfully synthesized before the completed structure of the natural material had been determined, and the molecule has been synthesized since by many different methods. Indeed it has more than once served as a model for the demonstration of new methods of peptide synthesis. The other mammalian kinins, kallidin and methionyl-lysyl-bradykinin, have been synthesized several times. Polistes kinin and phyllokinin, two kinins of nonmammalian origin, have also been synthesized. The structures of these peptides are given in Fig. 1.
This is a preview of subscription content, log in via an institution to check access.
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
Anastasi, A., Bertaccrni, G., Erspamer, V.: Pharmacological data on phyllokinin (bradykininyl-isoleucyl-tyrosine 0-sulphate) and bradykininyl-isoleucyl-tyrosine. Brit. J. Pharmacol. 27, 479 (1966).
Bernardi, L., Bosrsro, G., Decastiglione, R., Goffredi, O.: Synthesis of phyllokinin, a natural bradykinin analog. Experientia (Basel) 22, 425 (1966).
Boissonnas, R. A., Gutmann, S., Jacquenoud, P. A.: Synthèse de la L-arginyl-L-prolyl-L-prolyl-glycyl-phénylalanyl-L-seryl-L-prolyl-L-phénylalanyl-L-arginine, un nonapeptide présentant les propriétés de la bradykinine. Helv. chim. Acta 43, 1349 (1960).
Frmenv, M., Patchornik, A., Katchalski, E.: Use of polymers as chemical reagents. II. Synthesis of bradykinin. J. Amer. chem. Soc. 90, 2953 (1968).
Greenstein, J. P., Wurrz, M.: Chemistry of the amino acids. New York: Wiley 1961.
Gu’rm1ann, S., Pless, J., Bolssonnas, R. A.: Nouvelle synthèse de la bradykinine. Helv. chim. Acta 45, 170 (1962).
Lenard, J., Robinson, A. B.: Use of hydrogen fluoride in Merrifield solid phase peptide synthesis. J. Amer. chem. Soc. 89, 181 (1967).
Merrifiei.D, R. B.: Solid-phase peptide synthesis. III. An improved synthesis of bradykinin. Biochemistry (ACS) 3, 1385 (1964a).
Merrifiei.D, R. B.: Solid-phase peptide synthesis. IV. The synthesis of methionyl-lysyl-bradykinin. J. org. Chem. 29, 3100 (1964b).
Merrifiei.D, R. B.: Automatic synthesis of proteins. Sci. Amer., March 1968, p. 56.
Merrifiei.D, R. B., Srjwart, J. M.: Automated peptide synthesis. Nature (Lond.) 207, 522 (1965).
Merrifiei.D, R. B., Jernberg, N.: An instrument for automatic synthesis of peptides. Anal. Chem. 38, 1905 (1966).
Nicolames, E. D., Dewald, H. A.: Synthesis of polypeptides. Bradykinin J. org. Chem. 26, 3872 (1961).
Nicolames, E. D., Dewald, H. A., Mccarthy, D. A.: The synthesis of a biologically active decapeptide having the structure proposed for kallidin. II. Biochem. biophys. Res. Commun. 6, 210 (1961).
Pisano, J.: Vasoactive peptides in venoms. Fed. Proc. 27, 58 (1968).
Plebs, J., Stermer, E., Guttntann, S., Boissonnas, R. A.: Kallidin, Synthese und Eigenschaften. Helv. chim. Acta 45, 394 (1962).
Saraibara, S., Ibuxai, N.: The trifluoroacetate method of peptide synthesis. II. An improved synthesis of bradykinin. Bull. chem. Soc. Japan 39, 1567 (1966).
Schröder, E.: Über Peptidsynthesen. Synthese von Methionyl-Lysyl-Bradykinin, einem Kinin aus Rinderblut. Experientia (Basel) 20, 39 (1964).
Schröder, E., Gibian, H.: Synthese von Ornl-Kallidin und Kallidin. Ann. Chem. 673, 176 (1964).
Schröder, E., Litbke, K.: The peptides. New York: Academic Press 1965.
Shchurina, L. A., Ravdel, G. A., Filatova, M. P., Semxin, E. P., Keasnova, S. N.: Synthesis of bradykinin. Khim. Prirodn. Soedin. Akad. Nauk Uz. S.S.R. 2, 124 (1966).
Shchurina, L. A., Ravdel, G. A., Znuzz, A. L.: Depsipeptide analogs of biologically active peptides. II. Synthesis of bradykinin and its depsipeptide analogs. Acta chim. Acad. Sci. hung. 44, 205 (1965).
Sermon, I. Z.: New synthesis of bradykinin. Rocz. Chem. 38, 133 (1964).
Stewart, J. M.: Synthesis and pharmacology of polistes kinin, a bradykinin homolog. Fed. Proc. 27, 534 (1968)
Stewart, J. M., Woolley, D. W.: All-D-bradykinin and the problem of peptide antimetabolites. Nature (Lond.) 206, 619 (1965).
Stewart, J. M., Young, J. D.: Solid phase peptide synthesis. San Francisco: Freeman 1969.
Suzuki, K., Abixo, T., Asaka, M.: Synthesis of 4-L-leucine-6–0-acetyl-L-serine, 4-L-leucine, 6–0-acetyl-L-serine bradykinin, and bradykinin Chem. pharm. Bull. 14, 217 (1966).
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1970 Springer-Verlag Berlin · Heidelberg
About this chapter
Cite this chapter
Stewart, J.M. (1970). The Kinins: Methods of Chemical Synthesis. In: Erdös, E.G., Wilde, A.F. (eds) Bradykinin, Kallidin and Kallikrein. Handbook of Experimental Pharmacology / Handbuch der experimentellen Pharmakologie, vol 25 / 25. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46222-1_3
Download citation
DOI: https://doi.org/10.1007/978-3-642-46222-1_3
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-46224-5
Online ISBN: 978-3-642-46222-1
eBook Packages: Springer Book Archive