Multicomponent synthesis of tripeptides containing pipecolic acid derivatives: Selective induction of cis- And tmns-imide bonds into peptide backbones

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 12, 2000, Pages 1867-1871

  Maison, Wolfgang ^a   Lützen, Arne ^a   Kosten, Marc ^a   Sclilcmminger, Imre ^a   Westcrhoff, Ole ^a   Saak, Wolfgang ^a   Martens, Jürgen ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL BONDS; DERIVATIVES; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEINS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

MULTICOMPONENT SYNTHESIS;

POLYPEPTIDES;

EID: 0034697723     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002258f     Document Type: Article

References (27)

1. W. J. Wu and D. R. Raleigh, J. Org. Cliem., 1998, 63, 6689 and references 4-8 cited therein.
2. (a) C. Toniolo, Int. J. Peptide Protein Res., 1990, 35, 287;
3. (b) M. J. Genin, W. B. Gleason and R. L. Johnson, J. Org. Chem., 1993, 58, 860.
4. (a) Z. Zhao, X. Liu, Z. Shi, L. Danley, B. Huanc, R.-T. Jiang and M.-D. Tsai, J. Am. Chem. Soc., 1996, 118, 3535;
5. (b) D. Kern, M. Schutkovvski and T. Drakenberg, J. Am. Chem. Soc., 1997,119, 8403.
6. (a) G. D. Rose, L. M. Gierasch and J. A. Smith, Adv. Protein Chem. 1985, 37, 1;
7. (b) G. Müller, M. Gurrath and H. Kessler, Proteins: Struct. Fund. Genet., 1993,15, 235.
8. (a) G. Fischer and F. X. Schmid, Biochemistry, 1990, 29, 2205;
9. (b) S. M. Simon, C. S. Peskin and G. F. Oster, Proc. Nail. Acad. Sei. U.S.A. 1992,89, 3770.
10. (a) M. Soth and J. S. Nowick, J. Org. Chem., 1999, 64, 276;
11. (b) S. Hanessian, G. McNaughton-Smith, H.-G. Lombart and W. D. Lubell, Tetrahedron, 1997,53, 12789;
12. M.-J. Blanco, M. R. Paleo, C. Penide and F. J. Sardina, J. Org. Chem., 1999, 64, 8786.
13. (a) P. Dumy, M. Keller, D. E. Ryan, B. Rohwedder, T. Wöhr and M. Mutter, J. Am. Chem. Soc., 1997, 119, 918;
14. (b) E. Beausoleil, R. Sharma, S. W. Michnick and W. D. Lubell, J. Org. Chem., 1998, 63, 6572;
15. E. Beausoleil and W. D. Lubell, J. Am. Chem. Soc., 1996, 118, 12902 and references 2-10 cited therein;
16. N. G. Delaney and V. Madison, J. Am. Chem. Soc., 1982, 104, 6635;
17. (e) D. K. Chalmers and G. R. Marshall, J. Am. Chem. Soc., 1995, 117, 5927;
18. (f) C. Grathwohl and K. Lüthrich, Biopolymers 1981, 20, 2623.
19. W. Maison, A. Lützen, M. Kosten, I. Schlemminger, O. Westerhoff and J. Martens, J. Chem. Soc., Perkin Trans, 1, 1999, 3515.
20. L. Halab and W. D. Lubell, J. Org. Chem., 1999,64, 3312.
21. (a) M. Keller, C. Sager, P. Dumy, M. Schutkowski, G. S. Fischer and M. Mutter, J. Am. Chem. Soc., 1998, 120, 2714;
22. (b) M. Mutter, T. Wöhr, S. Gioria and M. Keller, Biopolymers, 1999,51, 121.
23. H. Zondler and W. Pfleiderer, Liebigs Ann. Client., 1972,759, 84.
24. W. Maison, M. Kosten, A. Charpy, J. Kintscher-Langenhagen, I. Schlemminger, A. Lützen, O. WesterhofT and J. Martens, EUT. J. Org. Chem., 1999, 2433.
25. J. R. Smolanoff (Rohm and Haas Co.), U.S. Pat. 2,756,360/1978 (Chem. Abstr., 1978,89, 124589f).
26. W. Maison, I. Schlemminger, O. Westerhoff and J. Martens, Bioorg. Med. Chem., in press.
27. T. E. Creighton, Proteins: Structures and Molecular Properties, 2nd edn., W. H. Freeman and Company, New York, 1993.