This paper dedicated to Dr. Shahriyar Omidvar for his effective contribution in Iranian pharmaceutical industry
Abstract
A highly efficient and practical synthesis of C-terminal amidated peptides has been developed. According to this approach, amidation of the C-terminus of peptides was carried out using NH4Cl, alkylammonium chloride (RNH3Cl) and semicarbazide hydrochloride in the presence of TBTU as a coupling reagent and a tertiary amine as the base at room temperature in good to high yields. Some opioid peptides such as enkephalin derivatives were synthesized according to this novel method.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J.B. Engel, R.S. Strutbers, in: B. Lunenfeld (Ed.), GnRH Analogs in Human Reproduction, Taylor & Francis, Wiltshire, UK, 2005, p. 35.
B.L. Wolozin, G.D. Pasternak, Proc. Natl. Acad. Sci. USA 78 (1981) 6181.
M. Kapuscinski, M. Green, S.N. Sinha, J.J. Shepherd, A. Shulkes, Clinical Endocrinol. 39 (1993) 51.
A. Martinez, A. Farr, M.D. Vos, F. Cuttitta, A.M. Treston, J. Histochem. Cytochem. 46 (1998) 661.
P.W. Schiller, in: S. Udenfriend, J. Meienhofer (Eds.), The Peptides: Analysis, Synthesis and Biology, Academic Press, Vol. 6, New York, 1984, p. 219.
V. Cerovsky, M.R. Kula, Angew. Chem. Int. Ed. 37 (1998) 1885.
H. Tamaoki, US Patent, 4,709,014, 1987.
H. Matsuo, K. Mizuno, M. Kojima, US Patent, 5,360,727, 1994.
C.T. Bui, A.M. Bray, T. Nguyen, F. Ercole, N.J. Maeji, J. Peptide Sci. 6 (2000) 243.
J.C. Kappel, G. Barany, J. Peptide Sci. 11 (2005) 525.
P. Stathopoulos, S. Papas, V. Tsikaris, J. Peptide Sci. 12 (2006) 227.
W.D. Kornreich, H.A. Anderson, J.S. Porter, E.F. Rivier, US Patent, 4,701,499, 1987.
D.P. Wolfe, J.C. Glorioso, D.J. Fink, WO/2006/132925.
S.A. Jackson, US Patent, 7,122,628 B2, 2006.
Y. Nishimura, Y. Suzuki, M. Tanihara, US Patent, 6,617,307 B1, 2003.
D.Y. Maeda, J.E. Ishmael, T.F. Murray, J.V. Aldrich, J. Med. Chem. 43 (2000) 3941.
T. Deeks, P.A. Crooks, R.D. Waigh, J. Med. Chem. 26 (1983) 762.
J. Hughes, T.W. Smith, H.W. Kosterlitz, L.A. Fothergill, B.A. Morgan, H.R. Morris, Nature 258 (1975) 577
H.B. Gutstein, H. Akil, in: L.L. Brunton, J.S. Lazo, K.L. Parker (nt(Eds.), Goodman & Gilman’s The Pharmacological Basis of Therapeutics, McGraw-Hill Companies, New York, 2006, p. 547.
G.B. Fiels, R.L. Noble, Int. J. Pept. Protein Res. 35 (1990) 161
K. Barlos, O. Chatzi, D. Gatos, G. Stavropulos, Int. J. Pept. Protein Res. 37 (1991) 513.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Arabanian, A., Mohammadnejad, M. & Balalaie, S. A novel and efficient approach for the amidation of C-terminal peptides. JICS 7, 840–845 (2010). https://doi.org/10.1007/BF03246077
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03246077