Rolling loop scan: An approach featuring ring-closing metathesis for generating libraries of peptides with molecular shapes mimicking bioactive conformations or local folding of peptides and proteins

Angewandte Chemie - International Edition

Volumn 38, Issue 24, 1999, Pages 3684-3687

  Reichwein, John F ^a   Wels, Bas ^a   Kruijtzer, John A W ^a   Versluis, Cees ^b   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b NONE

Author keywords

Combinatorial chemistry; Cyclizations; Peptides; Peptidomimetics; Ring closing metathesis

Indexed keywords

PEPTIDE LIBRARY;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; PEPTIDE SYNTHESIS; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE;

EID: 0033576637     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991216)38:24<3684::AID-ANIE3684>3.0.CO;2-M     Document Type: Article

References (23)

1. The presence of a number of disulfide bridges may give rise to formation of "cystine knots", providing absolute control over the three-dimensional structure. For a cystine knot in nerve growth factor, see N. Q. McDonald, R. Lapatto, J. Murray-Rust, J. Gunning, A. Wlodawer, T. L. Blundell, Nature 1991, 354, 411-414.
2. Sulfide bridges are present in lantibiotics; see, for example, D. Kaiser, R. W. Jack, G. Jung, Pure Appl. Chem. 1998, 70, 97-104.
3. For zinc fingers, see, for example, R. Kaptein, Curr. Opin Struct. Biol. 1991, 1, 63-70; R. Kaptein, Curr. Opin Struct. Biol. 1992, 2, 109-115.
4. For zinc fingers, see, for example, R. Kaptein, Curr. Opin Struct. Biol. 1991, 1, 63-70; R. Kaptein, Curr. Opin Struct. Biol. 1992, 2, 109-115.
5. A preeminent example of multiple side chain knotting is found in the vancomycin antibiotics; recent review: D. H. Williams, B. Bardsley, Angew. Chem. 1999, 111, 1264-1286; Angew. Chem. Int. Ed. 1999, 38, 1172-1193.
6. A preeminent example of multiple side chain knotting is found in the vancomycin antibiotics; recent review: D. H. Williams, B. Bardsley, Angew. Chem. 1999, 111, 1264-1286; Angew. Chem. Int. Ed. 1999, 38, 1172-1193.
7. Recent reviews: R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc. Perkin Trans. I 1998, 371-388.
8. Recent reviews: R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc. Perkin Trans. I 1998, 371-388.
9. For RCM involving side chains of amino acids, see a) S. J. Miller, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 5855-5856;
10. b) S. J. Miller, H. E. Blackwell, R. H Grubbs, J. Am. Chem. Soc. 1996, 118, 9606-9614;
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12. c) R. H. Grubbs, H. E. Blackwell, Angew. Chem. 1998, 110, 3469-3472; Angew. Chem. Int. Ed. 1998, 37, 3281-3284;
13. d) A. S. Ripka, R. S. Bohacek, D. H. Rich, Bioorg. Med. Chem. Lett. 1998, 8, 357-360;
14. e) J. Pernerstorfer, M. Schuster, S. Blechert, Chem. Commun. 1997, 1949-1950;
15. f) B. E. Fink, P. R. Kym, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1998, 120, 4334-4344;
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17. [6a,b]
18. J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246.
19. Although RCM can be carried out on the solid phase, so far higher yields were obtained if RCM was carried out in solution.
20. The studies which led to these rules will be published elsewhere. Not all sizes of loops are allowed, since in addition to steric factors imposed by the side chains, a peptide - amide bond usually assumes a trans-like conformation: J. F. Reichwein, C. Versluis, R. M. J. Liskamp, unpublished results.
21. Saponification of the methyl ester using Tesser's base (G. I. Tesser, I. C. Balvert-Geers, Int. J. Pept. Protein Res. 1975, 7, 295-305) is probably too harsh. Better results were obtained using the milder conditions of Corey et al. (E. J. Corey, I. Szekely, C. S. Shiner, Tetrahedron Lett. 1977, 3529-3532).
22. Saponification of the methyl ester using Tesser's base (G. I. Tesser, I. C. Balvert-Geers, Int. J. Pept. Protein Res. 1975, 7, 295-305) is probably too harsh. Better results were obtained using the milder conditions of Corey et al. (E. J. Corey, I. Szekely, C. S. Shiner, Tetrahedron Lett. 1977, 3529-3532).
23. Compounds 5-10 were obtained as cis/trans mixtures, which so far could not easily be separated by HPLC.