Abstract
As part of a program to prepare bradykinin (H-Arg-Pro-ProGly-Phe-Ser-Pro-Phe-Arg-OH) labelled at high specific radioactivities, we have synthesized three analogs for dehalogenation in tritium gas: [4-Br-Phe5]-bradykinin (BK), [4-Br-Phe8]-BK and [4-Br-Phe5,8]-BK. The analogs were synthesized by the Merrifield solid-phase method and were purified by molecular sieve and partition chromatography. The analogs themselves possess biological activity (as assayed for effects on mean arterial blood pressure and isolated rat uterus). [4-Br-Phe8]-BK was 1.5 to 3 times as active as bradykinin. [4-Br-Phe5,8]-BK was approx. 22% as active as BK and [4-Br-Phe5]-BK was approx. 18% as active. [4-Br-Phe5]-BK was submitted to catalytic dehalogenation with 10% Pd/C and 5% Rh/CaCO3 in H2O and DMF (1:1) plus 10 Ci of 3H2. [4-3H-Phe5]-BK was obtained at 6.7 Ci/mmole in an overall yield of 15%. [4-3HPhe8]-BK was prepared similarly to yield an intrinsically-labelled peptide with a specific radioactivity of 21 Ci/mmole.
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
Bergman, E.P., 1952, p-Amino-and p-fluoro-Ăź-phenylalanine, J. Amer. Chem. Soc., 74, 4947.
Brundish, D. and R. Wade, 1976, Tritiated peptides, Part 3, Synthesis of [4–3H-Phe7]-ß-corticotrophin-(1–24)-tetracosapeptide, J. Chem. Soc., Perkin I, 2186.
Chung, A., J.W. Ryan, P. Berryer and A. Day, 1978, Influence of phenylalanine residues on the activity of bradykinin, 176th Nat. Meet. Amer. Chem. Soc., Miami Beach, Sept. 9–15, 1978.
Dornow, A. and G. Winter, 1951, Some chloromycetin-like N-dichloroacetyl derivatives of the “phenylalaninol” series, Chem. Ber. 84, 307.
Eisen, V., Formation and functions of kinins, 1970, in: The Immunochemistry and Biochemistry of Connective Tissue and Its Disease States, Rheumatology, Vol. 3, (Karger Basel), p. 103.
Gisin, B.F., 1973, The preparation of Merrifield-resins through total esterification with cesium salts, Heiv. Chim. Acta, 56, 1476.
Houghten, R.A. and H. Rapoport, 1974, Synthesis of pure p-chlorophenyl-L-alanine from L-phenylalanine, J. Med. Chem., 17, 556.
Irreverre, F., 1965, A modified Sakaguchi spray, Biochim. Biophys. Acta, 111, 551.
Kaiser, LE., R.L. Colescott, C.D. Bossinger and P.I. Cook, 1970, Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides, Anal. Biochem, 34, 595.
Koenig, W. and R. Geiger, 1970, New method for the synthesis of peptides: Activation of the carboxyl group with dicyclohexylcarbodiimide by using 1-hydroxybenzoltriazoles as additives, Chem. Ber., 103, 788.
Roblero, J., J.W. Ryan and J.M. Stewart, 1973, Assay of kinins by their effects on blood pressure, Res. Commun. Chem. Path. Pharmac., 6, 207.
Ryan, J.W. and U.S. Ryan, 1977, Pulmonary endothelial cells, Fed. Proc., 36, 2683.
Ryan, U.S., J.W. Ryan, D. Habliston and G. Pena, Endothelial cells and components of the kallikrein-kinin system, this volume.
Sakakibara, S,, The use of hydrogen fluoride in peptide chemistry, 1971, in: Chemistry and Biochemistry of Amino Acids, ed. C.B. Weinstein ( Marcel Dekker, New York ), p. 51.
Schwyzer, R. and E. Surbeck-Wegmann, 1960, Resolution of D,L-pbromophenylalanine, Hely. Chim. Acta, 63, 1073.
Stewart, J.M. and J.D. Young, 1969, Solid Phase Peptide Synthesis, (W.H. Freeman Co., San Francisco).
Vine, W.H., D.A. Brueckner, P. Needleman, and G.R. Marshall, 1973, Synthesis, biological activity and 19F nuclear magnetic resonance spectra of angiotensin II analogs containing fluorine, Biochemistry, 12, 1630.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1979 Springer Science+Business Media New York
About this chapter
Cite this chapter
Chung, A., Ryan, J.W., Berryer, P., Block, R. (1979). Preparation of Intrinsically-Labelled Kinins. In: Fujii, S., Moriya, H., Suzuki, T. (eds) Kinins—II. Advances in Experimental Medicine and Biology, vol 120. Springer, New York, NY. https://doi.org/10.1007/978-1-4757-0926-1_5
Download citation
DOI: https://doi.org/10.1007/978-1-4757-0926-1_5
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4757-0928-5
Online ISBN: 978-1-4757-0926-1
eBook Packages: Springer Book Archive