Fmoc protected peptide mimetic based on a cyclohexane framework and incorporation into angiotensin II

Tetrahedron

Volumn 53, Issue 37, 1997, Pages 12497-12504

  Kühn, Christian ^a   Lindeberg, Gunnar ^b   Gogoll, Adolf ^c   Hallberg, Anders ^b   Schmidt, Boris ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b UPPSALA UNIVERSITY   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANGIOTENSIN II DERIVATIVE; CYCLOHEXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; REACTION ANALYSIS;

EID: 0343924186     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00779-5     Document Type: Article

References (18)

1. Middlemiss, D.; Watson, S. P. Tetrahedron 1994, 50, 13049-13080.
2. Moore, G. J.; Ganter, R. C.; Matsoukas, J. M.; Hondrelis, J.; Agelis, G.; Barlos, K.; Wilkinson, S.; Sandall, J.; Fowler, P. The importance of the aromatic ring quadrupole for receptor interactions of the position 4 side chains of angiotensin-II analogues. In Peptides: Chemistry, Structure and Biology; Hodges, R. S.; Smith, J. A. Eds.; ESCOM: Leiden, 1993; Vol. XIII; pp. 690-691.
3. Wexler, R. R.; Greenlee, W. J.; Irvin, J. D.; Goldberg, M. R.; Prendergast, K.; Smith, R. D.; Timmermans, P. B. M. W. M. J. Med. Chem. 1996, 39, 625-656.
4. Gante, J. Angew. Chem. 1994, 106, 1780-1802; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1672.
5. Gante, J. Angew. Chem. 1994, 106, 1780-1802; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1672.
6. Nikiforovich, G. V.; Marshall, G. R. Biochem. Biophys. Res. Commun. 1993, 195, 222-228.
7. Spear, K. L.; Brown, M. S.; Reinhard, E. J.; McMahon, E. G.; Olins, G. M.; Palomo, M. A.; Patton, D. R. J. Med. Chem. 1990, 33, 1935-1940.
8. Callahan, J. F.; Bates, J. W.; Burgess, J. L.; Eggleston, D. S.; Hwang, S. M.; Kopple, K. D.; Koster, P. F.; Nichols, A.; Peishoff, C. E.; Samanen, J. M.; Vasko, J. A.; Wong, A.; Huffman, W. F. J. Med. Chem. 1992, 35, 3970-3972, Newlander, K. A.; Callahan, J. F.; Moore, M. L.; Thomaszek Jr., T. A.; Huffman, W. F. J. Med. Chem. 1993, 36, 2321-2331.
9. Callahan, J. F.; Bates, J. W.; Burgess, J. L.; Eggleston, D. S.; Hwang, S. M.; Kopple, K. D.; Koster, P. F.; Nichols, A.; Peishoff, C. E.; Samanen, J. M.; Vasko, J. A.; Wong, A.; Huffman, W. F. J. Med. Chem. 1992, 35, 3970-3972, Newlander, K. A.; Callahan, J. F.; Moore, M. L.; Thomaszek Jr., T. A.; Huffman, W. F. J. Med. Chem. 1993, 36, 2321-2331.
10. Brickmann, K.; Somfai P.; Kihlberg, J. Tetrahedron Lett. 1997, 38, 3651-3654.
11. Huffman, W. F.; Callahan, J. F.; Codd, E. E.; Eggleston, D. S.; Lemieux, C.; Newlander, K. A.; Schiller, P. W.; Takata, D. T.; Walker, R. F. Mimics of Secondary Structural Elements of Peptides and Proteins. In Synthetic Peptides: Approaches to Biological Problems; Tam, J.; Kaiser, E. T. Eds.; AR. Liss: New York, 1989; pp. 257-266.
12. Huffman, W. F.; Callahan, J. F.; Eggleston, D. S.; Newlander, K. A.; Takata, D. T.; Codd, E. E.; Walker, R. F.; Schiller, P. W.; Lemieux, C.; Wire, W. S.; Burks, T. F. Reverse Turn Mimetics. In Peptides: Chemistry and Biology: Proceedings of the Tenth American Peptide Symposium; Marshall, G. R. Ed.; ESCOM: Leiden, 1988; pp. 105-108.
13. Callahan, J. F.; Bean, J. W.; Burgess, J. L.; Eggleston, D. S.; Hwang, S. M.; Kopple, K. D.; Foster, P. F.; Nichols, A.; Peishoff, C. E.; Samanen, J. M.; Vasko, J. A.; Wong, A.; Huffman, W. F. J. Med. Chem. 1992, 35, 3970-3972.
14. von Roedern, E. G.; Lohof, E.; Hessler, G.; Hoffmann, M.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 10156-10167.
15. Schmidt, B.; Lindman, S.; Tong, W.; Lindeberg, G.; Gogoll, A.; Lai, Z.; Thörnwall, M.; Synnergren, B.; Nilsson, A.; Welch, C. J.; Sohtell, M.; Westerlund, C.; Nyberg, F.; Karlén, A.; Hallberg, A. J. Med. Chem. 1997, 40, 903-919.
16. Engel, M.; Burris, C. W.; Slate, C. A.; Erickson, B. W. Tetrahedron 1993, 49, 8761-8770.
17. Kasina, S.; Nematollahi, J. Tetrahedron Lett. 1978, 16, 1403-1406.
18. Lampe, T. F. J.; Hoffmann, H. M. R.; Bornscheuer, U. T. Tetrahedron Asymm. 1996, 7, 2889-2900.