| Title | Solution synthesis of a potent cyclic amide-linked angiotensin II analogue, [Sar1,Lys3, Glu5] ANG II | |
| Authors | J. Ancans1, G.J. Moore², P. Roumelioti3 and J.M. Matsoukas3
1. Laboratory of Peptide Synthesis, Institute of Organic Synthesis, Riga, LV-1006, Latvia 2. Pharmacology and Therapeutics, University of Calgary, Alberta, Canada 3. Department of Chemistry, University of Patras, 265 00 Patra, Greece |
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| Citation | Ancans, J., Moore, G.J, Roumelioti, P., Matsoukas, J.M.: Solution synthesis of a potent cyclic amide-linked angiotensin II analogue, [Sar1,Lys3, Glu5] ANG II, Epitheorese Klin. Farmakol. Farmakokinet. 11(2-3): 108-112 (1997) | |
| Publication Date | 1997 | |
| Full Text Language | English | |
| Order – Buy | pharmakonpress[at]pharmakonpress[.]gr | |
| Keywords | Angiotensin II, cyclic amide-linked analogue, solution synthesis, activity. | |
| Other Terms | review article | |
| Summary | The amide finked cyclic Angiotensin II analogue, [Sar1,Lys3, Glu5] ANG II, has been synthesized by solution methodology and was found to be potent in the rat uterus assay: The cydization reaction performed with the pentafluorophenylester method at the tripeptide stage, proceeded fast with high yield and without formation of noticeable side products. In this study we describe the synthesis of the title analogue in which the central part of the molecule is fixed covalently in the conformation predicted according to the charge relay conformation model proposed for Angiotensin II (1-3). High reaction rate and yield in the cydization reaction may indicate an optimal proximity of these reacting groups for forming covalent linkage. | |
| References | 1. Matsoukas, J.M., Bigham, G., Zhou, N. and Moore, G.J.: H-NMR or [Sar¹] Angiotensin II conformation by nuclear Overhauser effect spectroscopy in the rotating frame (ROESY): clustering of aromatic rings in dimethyisuiphoxide. Peptides 11: 359-366 (1990)
2. Matsoukas, J.M., Hondrelis, J., Keramida, M., Mavromoustakos, T., Makriyannis, A., Yamdagni, R., Wu, Q. and Moore, G.J.: Role of the NH2-terminal domain of Angiotensin II and [Sar¹] Angiotensin II on conformation and activity: NMR evidence for aromatic ring clustering and peptide backbone folding compared to [Des ] Angiotensin II. J. Biol. Chem. 269: 5303-5312 (1994) 3. Matsoukas, J.M., Hondreiis, J., Agelis, G., Barios, K., Gatos, D., Ganter, R.C., Moore, D. and Moore, G.J.: Novel synthesis of cyclic amide-linked analogues of Angiotensin II and III. J. Med. Chem. 37: 2958-2669 (1994) 4. Ancans, J., Biseniece, D., Myshliakova, N., Porunkevich, E.A.: Cyclic analogues of Angiotensin II, with depressor and histamine-liberating activity. Bioorg. Khim. 12: 118-120 (1986) 5. Ancans, J., Biseniece, D., Myshliakova, N., Chipens, G. Synthesis and study of cyclic analogues of Angiotensin. Bioorg. Khim. 16: 358-369 (1990) 6. Biseniece, D., Ancans, J., Myshliakova, N., Kublis, G., Porunkevich, E. Synthesis and biological activity of cyclic analogues of Angiotensin. Bioorg. Khim. 13: 149-159 (1987) |
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Online ISSN 1011-6575
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