Effect of thioxopeptide bonds on α-helix structure and stability

Journal of the American Chemical Society

Volumn 130, Issue 25, 2008, Pages 8079-8084

  Reiner, Andreas ^a   Wildemann, Dirk ^b   Fischer, Gunter ^b   Kiefhaber, Thomas ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b MAX PLANCK RESEARCH UNIT FOR ENZYMOLOGY OF PROTEIN FOLDING   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; DICHROISM; HYDROGEN; NONMETALS; NUCLEAR MAGNETIC RESONANCE; OPTICAL PROPERTIES; PEPTIDES; PHOTOACOUSTIC EFFECT; PROTEINS; SYSTEM STABILITY;

CIRCULAR DICHROISM MEASUREMENTS; EXPERIMENTAL INVESTIGATIONS; GLYCINE (GLY); HELICAL STRUCTURES; HELIX STRUCTURES; HYDROGEN BONDINGS; ISOSTERIC; MODEL PEPTIDES; NMR CHARACTERIZATION; PHOTO-PHYSICAL PROPERTIES; PHYSICOCHEMICAL STUDIES; PROTEIN STRUCTURES; THIOAMIDE;

HYDROGEN BONDS;

ALANINE; AMIDE; GLYCINE; PEPTIDE DERIVATIVE; THIOXOAMIDE;

ALPHA HELIX; AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CIRCULAR DICHROISM; HYDROGEN BOND; MEASUREMENT; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; PROTEIN STABILITY; PROTEIN STRUCTURE;

AMINO ACID SEQUENCE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; THIOAMIDES;

EID: 45749156032     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8015044     Document Type: Article

References (47)

1. Baldwin, R. L. Biophys. Chem 2002, 101 (102), 203-210.
2. Baldwin, R. L. Weak interactions in protein folding: hydrophobic free energy, van der Waals interactions, peptide hydrogen bonds and peptide solvation. In Protein Folding Handbook; Buchner, J., Kiefhaber,T., Eds.; Wiley/VCH: Weinheim, 2005; Vol. 1, pp 127-162..
3. Ramachandran, G. N.; Sasisekharan, V. Adv. Protein Chem. 1968, 23, 283-437.
4. Flory, P. J. Statistical Mechanics of Chain Molecules; Hanser Publishers: Munich, 1969.
5. Krieger, F.; Möglich, A.; Kiefhaber, T. J. Am. Chem. Soc. 2005, 127, 3346-3352.
6. Seebach, D.; Ko, S. Y.; Kessler, H.; Köck, M.; Reggelin, M.; Schmieder, P.; Walkinshaw, M. D.; Bölsterli, J. J.; Bevec, D. Helv. Chim. Acta 1991, 74, 1953-1990.
7. Kessler, H.; Matter, H.; Geyer, A.; Diehl, H.-J.; Köck, M.; Kurz, G.; Opperdoes, F. R.; Callens, M.; Wierenga, R. K. Angew. Chem., Int. Ed. Engl. 1992, 31, 328-330.
8. Yao, S.; Zutshi, R.; Chmielewski, J. Bioorg. Med. Chem. Lett. 1998, 8, 699-704.
9. Frank, R.; Jakob, M.; Thunecke, F.; Fischer, G.; Schutkowski, M. Angew. Chem., Int. Ed. 2000, 39, 1120-1122.
10. Balaji, V. N.; Profeta, S.; Dietrich, S. W. Biochem. Biophys. Res. Commun. 1987, 145, 834-841.
11. Cour, T. F. M. Int. J. Peptide Protein Res. 1987, 30, 564-571.
12. Artis, D. R.; Lipton, M. A. J. Am. Chem. Soc. 1998, 120, 12200-12206.
13. Tran, T. T.; Treutlein, H.; Burgess, A. W. J. Comput. Chem. 2001, 22, 1026-1037.
14. Grabarse, W.; Mahlert, F.: Shima, S.; Thauer, R. K.; Ermler, U. J. Mol. Biol. 2000, 303, 329-344.
15. Aleman, C. J. Phys. Chem. A 2001, 105, 6717-6723.
16. Zhao, J.; Wildemann, D.; Jakob, M.; Vargas, C.; Schiene-Fischer, C. Chem. Commun. 2003, 2810-2811.
17. Wiberg, K. B.; Rush, D. J. J. Am. Chem. Soc. 2001, 123, 2038-2046.
18. Satzger, H.; Root, C.; Gilch, P.; Zinth, W.; Wildemann, D.; Fischer, G. J. Phys. Chem. B 2005, 109, 4770-4775.
19. Cervetto, V.; Bregy, H.; Hamm, P.; Helbing, J. J. Phys. Chem. A 2006, 110, 11473-11478.
20. Helbing, J.; Bregy, H.; Bredenbeck, J.; Pfister, R.; Hamm, P.; Huber, R.; Wachtveitl, J.; DeVico, L.; Olivucci, M. J. Am. Chem. Soc. 2004, 126, 8823-8834.
21. Wildemann, D.; Schiene-Fischer, C.; Aumüller, T.; Bachmann, A.; Kiefhaber, T.; Lücke, C.; Fischer, G. J. Am. Chem. Soc. 2007, 129, 4910-4918.
22. Miwa, J. H.; Patel, A. K.; Vivatrat, N.; Popek, S. M.; Meyer, A. M. Org. Lett. 2001, 3, 3373-3375.
23. Tran, T. T.; Zeng, J.; Treutlein, H.; Burgess, A. W. J. Am. Chem. Soc. 2002, 124, 5222-5230.
24. Miwa, J. H.; Pallivathucal, L.; Gowda, S.; Lee, K. E. Org. Lett. 2002, 4, 4655-4657.
25. Goodman, E. M.; Kim, P. S. Biochemistry 1991, 30, 11615-11620.
26. Marqusee, S.; Robbins, V. H.; Baldwin, R. L. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5286-5290.
27. Chakrabartty, A.; Schellman, J. A.; Baldwin, R. L. Nature 1991, 351, 586-588.
28. Scholtz, J. M.; Qian, H.; York, E. J.; Stewart, J. M.; Baldwin, R. L. Biopolymers 1991, 31, 1463-1470.
29. Scholtz, J. M.; Baldwin, R. L. Annu. Rev. Biophys. Biomol. Struct. 1992, 21, 95-118.
30. Chakrabartty, A.; Kortemme, T.; Baldwin, R. L. Protein Sci. 1994, 3, 843-852.
31. Rohl, C. A.; Chakrabartty, A.; Baldwin, R. L. Protein Sci. 1996, 5, 2623-2637.
32. Lifson, S.; Roig, A. J. Chem. Phys. 1961, 34, 1963-1974.
33. Hollósi, M.; Kollát, E.; Kajtár, J.; Kajtár, M.; Fasman, G. D. Biopolymers 1990, 30, 1061-1072.
34. Luo, P.; Baldwin, R. L. Biochemistry 1997, 36, 8413-8421.
35. Doig, A. J.; Chakrabartty, A.; Klingler, T. M.; Baldwin, R. L. Biochemistry 1994, 33, 3396-3403.
36. Shoemaker, K. R.; Kim, P. S.; York, E. J.; Stewart, J. M.; Baldwin, R. L. Nature 1987, 326, 563-567.
37. Scherer, G.; Kramer, M. L.; Schutkowski, M.; Reimer, U.; Fischer, G. J. Am. Chem. Soc. 1998, 120, 5568-5574.
38. Jensen, O. E.; Lawesson, S.-O.; Baadi, R.; Piazzesi, A. N.; Toniolo, C. Tetrahedron 1985, 41, 5595-5606.
39. Millhauser, G. L.; Stenland, C. J.; Hanson, P.; Bolin, K. A.; van de Ven, F. J. J. Mol. Biol. 1997, 267, 963-974.
40. Merutka, G.; Dyson, H. J.; Wright, P. E. J. Biomol. NMR 1995, 5, 14-24.
41. Cierpicki, T.; Otlewski, J. J. Biomol. NMR 2001, 21, 249-261.
42. Wuthrich, K.; Billeter, M.; Braun, W. J. Mol. Biol. 1984, 180, 715-740.
43. Bolin, K. A.; Millhauser, G. L. Acc. Chem. Res. 1999, 32, 1027-1033.
44. Blaber, M.; Zhang, X. J.; Matthews, B. W. Science 1993, 260, 1637-1640.
45. Sánchez, I. E.; Kiefhaber, T. J. Mol. Biol. 2003, 334, 1077-1085.
46. Wildemann, D.; Drewellow, M.; Fischer, G.; Schutkowski, M. Chem. Commun. 1999, 1809-1810.
47. Fasman, G. D. Handbook of Biochemistry and Molecular Biology, 3rd ed.; CRC Press: 1976; p 186.