Lanthanide(III) complexes with two hexapeptides incorporating unnatural chelating amino acids: Secondary structure and stability

Chemistry - A European Journal

Volumn 15, Issue 30, 2009, Pages 7456-7469

  Cisnetti, Federico ^a   Gateau, Christelle ^a   Lebrun, Colette ^a   Delangle, Pascale ^a  

^a CNRS   (France)

Author keywords

Amino acids; Bioinorganic chemistry; Lanthanides; Peptides; Structure elucidation

Indexed keywords

BINDING PEPTIDE; BIOINORGANIC CHEMISTRY; CARBON ATOMS; CIRCULAR DICHROISM; COMPLEXATION PROPERTIES; ENANTIOPURE; HEXAPEPTIDES; LANTHANIDE; LANTHANIDE COMPLEX; LANTHANIDES; MONONUCLEAR COMPLEXES; NMR SPECTRUM; ORDERS OF MAGNITUDE; PEPTIDE SECONDARY STRUCTURES; SECONDARY STRUCTURES; SIDE CHAINS; SIDE-CHAIN; SOLID PHASE PEPTIDE SYNTHESIS; SOLUTION NMR; STABILITY CONSTANTS; STRUCTURE ELUCIDATION; SYNTHONS; TYPE II;

ADA (PROGRAMMING LANGUAGE); AMINATION; AMINO ACIDS; BIOCHEMISTRY; CHELATION; CIRCULAR DICHROISM SPECTROSCOPY; COMPLEXATION; DICHROISM; MASS SPECTROMETRY; METAL COMPLEXES; METAL IONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; PEPTIDES; RARE EARTH ELEMENTS; SYNTHESIS (CHEMICAL);

AMINES;

AMINO ACID; LANTHANIDE; METALLOPROTEIN; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACIDS; LANTHANOID SERIES ELEMENTS; MAGNETIC RESONANCE SPECTROSCOPY; METALLOPROTEINS; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 67651055376     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900747     Document Type: Article

References (86)

1. E. Pidcock, G. R. Moore, J. Biol, lnorg. Chem. 2001, 6, 479-489.
2. P. Caravan, J. J. Ellison, T. J. McMurry, R. B. Lauffer, Chem. Rev. 1999, 99, 2293-2352.
3. a) A. E. Merbach, E. Toth, The Chemistry of Contrast Agents, Wiley, New York. 2001;
4. b) S. Aime, M. Botta, E. Terreno, Adv. Inorg. Chem. 2005, 57, 173-237;
5. c) P. Caravan, Chem. Soc. Rev. 2006, 35, 512-523.
6. a) C. Piguet, C F. G. C. Geraldes in Handbook on the Physics and Chemistry of Rare Earths (Eds.: K.A.J. Gschneidner, J.-C. G. Bünzli, V. K. Pecharsky). Elsevier, 2003, pp. 353-463;
7. b) L. Di Bari, P. Salvadoři. Coord. Chem. rev. 2005, 249, 2854-2879.
8. G. Otting, J. Biomol. NMR 2008, 42, 1-9.
9. a)J.-C. Bünzli, C. Piguet, Chem. Soc. Rev. 2005, 34, 1048-1077;
10. b) J.-C. G. Bünzli, Acc. Chem. Res. 2006, 39, 53-61:
11. c) S. Pandya, J. Yu, D. Parker, Dalton Trans. 2006, 2757-2766.
12. a) J. P. MacManus, C. W. Hogue, B. J. Marsden. M. Sikorska, A. G. Szabo, J. Biol. Chem. 1990, 265, 10358-10366;
13. b) C. W. Hogue, J. P. MacManus, D. Banville, A. G. Szabo, J. Biol. Chem. 1992, 267, 13340-13347.
14. a) R. T. Kovacic, J. T. Welch, S. J. Franklin, J. Am. Chem. Soc. 2003, 125, 6656-6662;
15. b) P. Caravan, J. M. Greenwood, J. T. Welch. S.J. Franklin, Chem. Commun. 2003, 2574-2575.
16. a) M. Nitz, K.J. Franz, R. L. Maglathlin, B. Tmperiali. ChemBioChem 2003, 4, 272-276;
17. b) K.J. Franz, M. Nitz, B. Imperiali, ChemBioChem 2003, 4, 265-271.
18. M. Nitz. M. Sherawat. K. J. Franz, E. Peisach, K. N. Allen, B. Imperiali, Angew. Chem. 2004, 116, 3768-3771;
19. Angew. Chem. Int. Ed. 2004, 43, 3682-3685.
20. C. S. Bonnet, P. H. Fries. S. Crouzy, O. Sénèque, F. Cisnelti, D. Boluryn, P. Dumy, P. Delangle, Chem. Eur. J. 2009, DOI: 10.1002/chem.200900636.
21. a) I. D. Clark, I. Hill. M. Sikorska-Walker. J. P. MacManus, A. G.
22. Szabo, FEBS Lett. 1993, 333, 96-98;
23. b) A. M. Reynolds, B. R. Sculimbrene, B. Imperiali, Bioconjugate. Chem. 2008, 19, 588-591;
24. c) C. S. Bonnet. M. Devocelle, T. Gunnlaugsson. Chem. Commun. 2008, 4552-4554.
25. R. P. Cheng. S. L. Fisher, B. Imperiali, J. Am. Chem. Soc. 1996, 118, 11349-11356.
26. a) M. D. Shults, D. A. Pearce, B. Imperiali. J. Am. Chem. Soc. 2003, 125, 10591-10597;
27. b) H. Ishida, M. Kyakuno, S. Oishi, Biopolymers 2004, 76. 69-82.
28. a) M. R. Ghadiri, C. Soares, C. Choi, J. Am. Chem. Soc. 1992, 114, 825-831:
29. b) M. R. Ghadiri, M. A. Case, Angew. Chem. 1993, 105, 1663-1670:
30. Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597;
31. c) A. J. Doerr. G. L. McLendon, Inorg. Chem. 2004, 43, 7916-1925.
32. a) W. D. Kohn, C. M. Kay, B. D. Sikes, R. S. Hodges. J. Am. Chem. Soc. 1998, 120, 1124-1132:
33. b) A. Kashiwada, K. Ishida, K. Matsuda, Bull. Chem. Soc. Jpn. 2007, 80, 2203-2207.
34. F. Ruan, Y Chen, K. ltoh. T. Sasaki, RB. Hopkins. J. Org. Chem. 1991, 56, 4347-4354.
35. W. M. Kazmierski, Int. J. Pept. Protein Res. 1995, 445, 241-247.
36. S. Hulschenreiter. L. Neumann, U. Radler, L. Schmitt. R. Tampe, ChemBioChem 2003, 4, 1340-1344.
37. F. Q. Rúan. Y. O. Chen, P. B. Hopkins, J. Am. Chem. Soc. 1990, 112, 9403-9404.
38. R. H. Holm, P. Kennepohl, E.I. Solomon. Chem. Rev. 1996, 96, 2239-2314.
39. J. A. Smith, L. G. Pease. Crit. Rev. Biochem. 1980, 8, 315-399.
40. F. Filira. B. Biondi. L. Biondi, E. Giannini, M. Gobbo, L. Negri. R. Rocchi, Org. Biomol. Chem. 2003, 1. 3059-3063.
41. Y. Huang, S. Dey. X. Zhang, F. Sünnichsen, P. Garner, J. Am. Chem. Soc. 2004, 126, 4626-4640.
42. A. F. Abdel-Magid, S. J. Mehrman, Org. Process Res. Dev. 2006, 10, 971-1031.
43. O. V. Larionov. A. de Meijere, Org. Lett. 2004, 6, 2153-2156.
44. a) F. J. Blanco, G. Rivas, L. Serrano. Nat. Struct. Biol. 1994, 1, 584-590;
45. b) J. Venkalraman. S. C. Shankaramma, P. Balaram. Chem. Rev. 2001, 101, 3131-3152:
46. c) R. M. Hughes, M. L. Waters, Curr. Opin. Struct. Biol 2006, 16, 514-524.
47. A. M. C. Marcelino, L. M. Gierasch. Bhpolymers 2008, 89, 380-391.
48. S. R. Ragholhama, S. K. Awaslhi. P. Balaram, J. Chem. Soc. Perkin Trans. 2 1998, 137-143.
49. A. Borics. R. F. Murphy. S. Lovas. J. Biomo!. Struct. Dyn. 2004, 22, 761-770.
50. B. P. Joshí, K.-H. Lee, Bioorg. Med. Chem. 2008, 16, 8501-8509.
51. W. C. Chan, P. D. White, Fmoc Solid Phase Peptide Synthesis-A Practical Approach, OUP, Oxford. 2000.
52. K. Wülhrich, NMR of Proteins and Nucleic Acids, Wiley. New York. 1986.
53. R. M. Smith, A. E. Martell, R. J. Motekaitis, NIST Critically Selected Stability Constants of Metal Complexes Database, NlST Standard Reference Database 46, 2001.
54. V. B. Di Marco, G. G. Bombi, Mass. Spectrom. Rev. 2006, 25, 347-379.
55. N. Sreerama. R. W. Woody in Circular Dichroism, Principles and Applications. 2nd ed. (Eds.: N. Berova. K. Nakanishi, R. W. Woody), Wiley, New York, 2000, pp. 601 -620.
56. A. Perczel, M. Hollósi in CD and the Conformational Analysis of Biomotecules (Ed.: G. D. Fasman), Plenum Press, New York, 1996, pp. 285-380.
57. R. W. Woody. A. K. Dunker in CD and the Conformational Analysis of Biomotecules (Ed.: G. D. Fasman), Plenum Press, New York, 1996, pp. 109-157.
58. P. D. Adams. Y. Chen, K. Ma, M. G. Zagorsky, F. D. Sönnichsen, M. L. McLaughlin, M. D. Barkley, J. Am. Chem. Soc. 2002, 124, 9278-9286.
59. a) W. De Horrocks, W. E. Collier, J. Am. Chem. Soc. 1981, 103, 2856-2862:
60. b) P.J. Breen, E. K. Hild, W. DeW. Horrocks. Biochemistry 1985, 24, 4991 -4997.
61. W. De Horrocks, D. R. Sudnick. Acc. Chem. Res. 1981, 14, 384-392.
62. A. Beeby, I. M. Clarkson, R. S. Dickins, S. Faulkner, D. Parker. L. Royle. A. S. de Sousa. J. A. G. Williams. M. Woods, J. Chem. Soc. Faraday Trans. 2 1999, 493-503.
63. W. De Horrocks, D. R. Sudnick, J. Am. Chem. Soc. 1979, 101, 334-340.
64. a) N. Ouali, J.-P. Riviera, D. Chapon, P. Delangle. C. Piguet, lnorg. Chem. 2004, 43, 1517-1529:
65. b) L. Di Bari, M. Lelli, G. Pintacuda, G. Pescitelli, F. Marchetti, P. Salvadoři, J. Am. Chem. Soc. 2003, 125, 5549-5558.
66. M. Heitzmann, F. Bravard, C. Gateau, N. Boubals, C. Berthon, J. Pecaut, M. C. Charbonnel. P. Delangle, Inorg. Chem. 2009, 48, 246-256.
67. D. Neuhaus, Nuclear Overhuuser Effect in Structure & Conformational Analysis of Biomotecules, Wiley, New York, 2000.
68. a) A. T. Brunger, Nat. Protoč. 2007, 2, 2728-2733;
69. b) A. T. Brünger. P. D. Adams, G. M. Clorec. W. L. DeLano. P. Grose, R. W. GrosseKunstleve. J.-S. Jiang, J. Kuszewski, M. Nilges. N. S. Pannu, R. J. Read, L. M. Rice, T. Simonson, G. L. Warren, Acta Crystaltogr. Sect. D1998, 54, 905-921.
70. J. T. Welch, W. R. Kearney, S. J. Franklin, Proc. Natl. Acad. Sci. USA 2003, 100, 3725-3730.
71. R. Bhatlacharyya, P. Chakrabarli, J. Mot. Biol. 2003, 331, 925-940.
72. a) T. Yamamura, T. Watanabe. A. Kikuchi, T. Yamane, M. Ushiya-ma, H. Hirola. Inorg. Chem. 1997, 36, 4849-4859;
73. b) O. Sénèque, S. Crouzy, D. Boturyn, P. Dumy, M. Ferrand, P. Delangle, Chem. Commun. 2004, 770-771;
74. c) P. Rousselot-Pailley, O. Seneque, C. Lebrun, S. Crouzy, D. Boturyn, P. Dumy, M. Ferrand. P. Delangle, Inorg. Chem. 2006, 45, 5510-5520.
75. a) H. N. Hoang, G. K. Bryant, M. J. Kelso, R. L. Beyer, T. G. Appleton, D. P. Fairlie. Inorg. Chem. 2008, 47, 9439-9449;
76. b) R. L. Beyer, H. N. Hoang, T. G. Appleton, D. P. Fairlie, J. Am. Chem. Soc. 2004, 126, 15096-15105.
77. W. S. Hancock, J. E. Battersby, Anal. Bhchem. 1976, 71, 260-264.
78. a) H. Gampp, M. Maeder. C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 95-101;
79. b) H. Gampp. M. Maeder, C. J. Meyer, A. D. ZuberbUhler, Talanta 1985, 32, 257-264:
80. c) H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 1133-1139;
81. d) H. Gampp, M. Maeder, C. J. Meyer, A. D. ZuberbUhler, Talanta 1986, 33, 943-951.
82. I. J. Bruno, J. C. Cole. P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor. Acta Crystaltogr. Sect. B 2002, 58, 389-397.
83. R. D. Shannon, Acta Crystaltogr. Sect. A 1976, 32, 751-767.
84. C. Pérez. F. Löhr, H. Rüterjans, J. M. Schmidt, J. Am. Chem. Soc. 2001, 123, 7081-7093.
85. C. M. Fletcher, D. N. M. Jones, R. Diamond, D. Neuhaus, J. Biomol. NMR 1996, 8, 292-310.
86. W. L. Delano. The PyMOL Molecular Graphics System, Delano Scientific. Palo Alto, USA. 2002. http://www.pymol.org/