Pseudo-prolines: Induction of cis/trans-conformational interconversion by decreased transition state barriers

Biopolymers - Peptide Science Section

Volumn 51, Issue 2, 1999, Pages 121-128

  Mutter, Manfred ^a   Wöhr, Torsten ^a   Gioria, Séverine ^a   Keller, Michael ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Cis trans isomerization; Cyclophilin A; Polyproline helices I and II; Pro rich peptides; Pseudo prolines

Indexed keywords

BIOCONVERSION; CHEMICAL BONDS; CONFORMATIONS; ISOMERIZATION; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; PROTEINS; REACTION KINETICS; THERMODYNAMICS;

BIOSTRUCTURE;

POLYPEPTIDES;

4 NITROANILINE; CHYMOTRYPSIN; CYCLOPHILIN A; CYCLOSPORIN A; FK 506 BINDING PROTEIN; PARVULIN; PEPTIDE; PROLINE DERIVATIVE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CIS TRANS ISOMERISM; CONFORMATIONAL TRANSITION; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; THERMODYNAMICS; X RAY ANALYSIS;

CHYMOTRYPSIN; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; ISOMERISM; KINETICS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PEPTIDES; PROLINE; PROTEIN STRUCTURE, SECONDARY; PROTEINS; THERMODYNAMICS;

EID: 0032801691     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0282(1999)51:2<121::AID-BIP2>3.0.CO;2-O     Document Type: Article

References (37)

1. (a) Gratwohl, C.; Wüthrich, K. Biopolymers 1996, 15, 2025-2041.
2. (b) Gratwohl, C.; Wüthrich, K. Biopolymers 1981, 20, 2623-2633.
3. (c)Schmid, F.X.; Mayr, L.M.; Mückle, M.; Schönbrunner, E.R. Adv Protein Chem 1993, 44, 25-66.
4. Wüthrich, K.; Billeter, M.; Braun, W. J Mol Biol 1984, 180, 715-740.
5. Tweedy, N. B.; Nair, S. K.; Paterno, S. A.; Fierke, C.A.; Christianson, D. W. Biochemistry 1993, 32, 10944-10949.
6. Simon, S. M.; Peskin, C. S.; Oster, G. F. Proc Natl Acad Sci USA 1992, 89, 3770-3774.
7. Kautz, R. A.; Fox, R. O. Protein Sci 1993, 2, 851-858.
8. (a) Jackson, S. E.; Fersht, A. R. Biochemistry 1991, 30, 10436-10443.
9. (b) Tan, Y.-J.; Oliveberg, M.; Otzen, D.E.; Fersht, A. R. J Mol Biol 1997, 269, 611-622.
10. (a) Kautz, R. A.; Fox, R. O. Protein Sci 1993, 2, 851-858.
11. (b) Plaxco, K. W.; Spitzfaden, C.; Campbell, I .D.; Dobson, C. M. Proc Natl Acad Sci USA 1996 93, 10703-10706.
12. Fischer, S.; Dunbrack, R. L., Jr.; Karplus, M. J Am Chem Soc 1994, 116, 11931-11937.
13. Reimer, U.; El Mokdad, N.; Schutkowski, M.; Fischer, G. Biochemistry 1997, 36, 13802-13808.
14. Wöhr, T.; Wahl, F.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X.; Mutter, M. J Am Chem Soc 1996, 119, 918-925.
15. (a) Haack, T.; Mutter, M. Tetrahedron Lett 1992, 33 (12), 1589-1592.
16. (b) Wöhr, T.; Mutter, M. Tetrahedron Lett 36, 3847-3848 (1995).
17. (c)Wöhr, T.; Nefzi, A.; Sato, T.; Sun, X.; Wahl, F.; Mutter, M. Pept Res 1995, 8 (3) 145-153.
18. Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J Am Chem Soc 1998, 120, 2714-2720.
19. Fischer, G. S. Angew Chem, Int Ed Engl 1994, 33, 1415-1436.
20. Rahfeld, J.-U.; Schierhorn, A.; Mann, K.; Fischer, G. FEBS Lett 1994, 343, 65-69.
21. (a) Pawson, T. Nature 1995, 373, 573-580.
22. (b) Cohen, G. B.; Ren, R.; Baltimore, D. Cell 1995, 80, 237-248.
23. Ren, R.; Mayer, B.J.; Cicchetti, P.; Baltimore, D. Science 1993, 259, 1157-1161.
24. Dalgarno, D. C.; Botfield, M. C.; Rickles, R. J. Pept Sci 1998, 43 (5), 383-400.
25. Fischer, G. S.; Bang, H.; Mech, C. Biomed Biochim Acta 1984, 43, 1101.
26. Preliminary measurements on 2-C(R) monosubstituted ΨPro revealed a slightly increased first-order rate constant compared to the 2-C(S) analogue. However, due to low accuracy, an interpretation of these findings cannot be given.
27. Nefzi, A.; Schenk, K.; Mutter, M. Protein Pept Lett 1994, 1, 66-69.
28. H,Hpro)-NHMe reveals a distance of the tertiary amide bond of 1.33 Å.
29. (a) Berger, A.; Kurtz, J.; Katchalski, E. J Am Chem Soc 1954, 76, 5552-5553.
30. (b) Traub, W.; Shmueli, V. Nature 1963, 198, 1165-1166.
31. (c)Sasisekharan, V. Acta Crystallogr 1959, 12, 897-903.
32. (d)Cowan, P. M.; McGavin, S. Nature 1955, 176, 501-503.
33. (a) Rabanal, R.; Ludevid, M.-D.; Pons, M.; Giralt, E. J Org Chem 1993, 61, 6775-6781.
34. (b) Krimm, S.; Ronish, E W. Biopolymers 1974, 13, 1635-1651.
35. Lin, L-N.; Brandts, J. Biochemistry 1980, 19, 3055-3059.
36. Thomasson, K. A.; Applequist, J. Biopolymers 1991, 31, 529-535.
37. Fischer, S.; Dunbrack, Jr.; Karplus, M. J Am Chem Soc 1994, 116, 11931-11937.