Aryldithioethyloxycarbonyl (Ardec): A new family of amine protecting groups removable under Mild reducing conditions and their applications to peptide synthesis

Chemistry - A European Journal

Volumn 12, Issue 13, 2006, Pages 3655-3671

  Lapeyre, Milaine ^a   Leprince, Jérôme ^b   Massonneau, Marc ^c   Oulyadi, Hassan ^a   Renard, Pierre Yves ^a   Romieu, Anthony ^a   Turcatti, Gerardo ^d   Vaudry, Hubert ^b  

^a UNIVERSITÉ DE ROUEN   (France)

^b INSERM   (France)

^c QUIDD   (France)

^d Manteia Predictive Medicine SA   (Switzerland)

Author keywords

Enzymes; Fluorescent probes; FRET (fluorescence resonance energy transfer); Peptides; Protecting groups; Solid phase synthesis

Indexed keywords

AMINO ACIDS; CHEMICAL MODIFICATION; ENZYMES; SUBSTRATES; SYNTHESIS (CHEMICAL);

FLUORESCENCE RESONANCE ENERGY TRANSFER (FRET); FLUORESCENT PROBES; PEPTIDES; PROTECTING GROUPS; SOLID-PHASE SYNTHESIS;

AMINES;

AMINE; LYSINE; PEPTIDE; THIOL DERIVATIVE; URETHAN;

ARTICLE; BIOCHEMISTRY; CHEMISTRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; METHODOLOGY; SOLUTION AND SOLUBILITY; SYNTHESIS;

AMINES; BIOCHEMISTRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; LYSINE; PEPTIDES; SOLUTIONS; SULFHYDRYL COMPOUNDS; URETHANE;

EID: 33646184196     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501538     Document Type: Article

References (95)

1. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999.
2. P. Kocienski, Protecting Groups. 3rd ed., Thieme, Stuttgart, 2003.
3. P. R. Iyer, S. L. Beaucage in Comprehensive Natural Products Chemistry, Vol. 7 (Ed.: E. T. Kool), Pergamon Press, Amsterdam, 1999, pp. 105-152.
4. Y. Komatsu, E. Ohtsuka in Comprehensive Natural Products Chemistry, Vol. 6 (Eds.: D. Söll, S. Nishimura, P. B. Moore), Pergamon Press, Oxford, 1999, pp. 81-96.
5. P. M. Collins, R. J. Ferrier, Monosaccharides: Their Chemistry and Their Roles in Natural Products, Wiley, Chichester, 1995.
6. N. Sewald, H.-D. Jakubke, Peptides: Chemistry and Biology, Wiley, Weinheim, 2002.
7. D. Kadereit, H. Waldmann, Chem. Rev. 2001, 101, 3367-3396.
8. F. Guibé, Tetrahedron 1998, 54, 2967-3042.
9. D. R. Crouch, Tetrahedron 2004, 60, 5833-5871.
10. a) C. G. Bochet, J. Chem. Soc. Perkin Trans, 1 2002, 125-142;
11. b) C. G. Bochet, Synlett 2004, 2268-2274.
12. As illustrated by the thiol-labile cysteine protecting groups for peptide synthesis: 3-nitro-2-pyridinesulfenyl (Npys), S-methyloxycarbonylsulfenyl (Scm), S-[(N′-methyl-N-phenylcarbamoylsulfenyl] (Snm) and S-(tert-butylthio (StBu); for a review, see : I. Annis, B. Hargittai, G. Barany, Methods Enzymol. 1997, 289, 198-221.
13. a) G. Barany, R. B. Merrifield, J. Am. Chem. Soc. 1977, 99, 7363-7365;
14. b) G. Barany, F. Albericio, J. Am. Chem. Soc. 1985, 107, 4936-4942.
15. M. Planas, E. Bardají, K. J. Jensen, G. Barany, J. Org. Chem. 1999, 64, 7281-7289.
16. M. J. Barany, R. P. Hammer, R. B. Merrifield, G. Barany, J. Am. Chem. Soc. 2005, 127, 508-509.
17. M. Kwiatkowski (Quiatech AB), WO0125247, 2001.
18. For other examples of 3′-O-blocked fluorescent nucleoside triphosphates designed for DNA sequencing by synthesis, see: a) H. Ruparel, L. Bi, Z. Li, X. Bai, D. H. Kim, N. J. Turro, J. Ju, Proc. Natl. Acad. Sci. USA 2005, 102, 5932-5937;
19. b) M. B. Welch, C. I. Martinez, A. J. Zhang, S. Jin, R. Gibbs, K. Burgess, Chem. Eur. J. 1999, 5, 951-960.
20. C. Schultz, Bioorg. Med. Chem. 2003, 11, 885-898.
21. J. P. Parrish, R. N. Salvatore, K. W. Jung, Tetrahedron 2000, 56, 8207-8237.
22. For recent publications reporting the use of a 4-nitrophenyl carbonate derivative to introduce a new N-protecting group on amino acids, see: a) K. Hojo, M. Maeda, K. Kawasaki, Tetrahedron Lett. 2004, 45, 9293-9295;
23. b) K. Hojo, M. Maeda, K. Kawasaki, Tetrahedron 2004, 60, 1875-1886;
24. c) I. Lingard, G. Bhalay, M. Bradley, Synlett 2003, 1791-1792.
25. a) H. Salo, A. Guzaev, H. Lönnberg, Bioconjugate Chem. 1998, 9, 365-371;
26. b) N. Murthy, J. Campbell, N. Fausto, A. S. Hoffman, P. S. Stayton, Bioconjugate Chem. 2003, 14, 412-419.
27. L. Field, T. F. Parsons, D. E. Pearson, J. Org. Chem. 1966, 31, 3550-3555.
28. D. Moran, K. Sukcharoenphon, R. Puchta, H. F. Schaefer, III, P. v. R. Schleyer, C. D. Hoff, J. Org. Chem. 2002, 67, 9061-9069.
29. A. Rosowsky, J. E. Wright, J. Org. Chem. 1983, 48, 1539-1541.
30. L. Lapatsanis, G. Milias, K. Froussios, M. Kolovos, Synthesis 1983, 671-673.
31. For a recent review on peptide coupling reagents, see: S.-Y. Han, Y.-A. Kim, Tetrahedron 2004, 60, 2447-2467.
32. Results from these solution assays are also summarized in a table available in Supporting Information.
33. a, data in water at 25 °C (calculated using Advanced Chemistry Development (ACD/Labs) Software Solaris V4.67) for 2-mercaptoethyl methyl carbamate: 9.25 ± 0.25.
34. D. W. Nicholson, A. Ali, N. A. Thornberry, J. P. Vaillancourt, C. K. Ding, M. Gallant, Y. Gareau, P. R. Griffin, M. Labelle, Y. A. Lazebnik, N. A. Munday, S. M. Raju, M. E. Smulson, T.-T. Yamin, V.-L. Yu, D. K. Miller, Nature 1995, 376, 37-43.
35. For reviews on caspases, see: a) J.-B. Denault, G. S. Salvesen, Chem. Rev. 2002, 102, 4489-4499;
36. b) M. Donepudi, M. G. Grütter, Biophys. Chem. 2002, 101-102, 145-153;
37. c) H. R. Stennicke, G. S. Salvesen, Cell Death Differ. 1999, 6, 1054-1059.
38. S. Kothakota, T. Azuma, C. Reinhard, A. Klippel, J. Tang, K. Chu, T. J. McGarry, M. W. Kirschner, K. Koths, D. J. Kwiatkowski, L. T. Williams, Science 1997, 278, 294-298.
39. For reviews on caspase inhibitors, see: a) M. E. Nuttall, D. Lee, B. McLaughlin, J. A. Erhardt, Drug Discovery Today 2001, 6, 85-91;
40. b) R. V. Talanian, K. D. Brady, V. L. Cryns, J. Med. Chem. 2000, 43, 3351-3371.
41. M. A. O'Brien, W. J. Daily, P. E. Hesselberth, R. A. Moravec, M. A. Scurria, D. H. Klaubert, R. F. Bulleit, K. V. Wood. J. Biomol. Screening 2005, 10, 137-148.
42. S. M. Gopalakrishnan, J. Karvinen, J. L. Kofron, D. J. Burns, U. Warrior, J. Biomol. Screening 2002, 7, 317-323.
43. M. Preaudat, J. Ouled-Diaf, B. Alpha-Bazin, G. Mathis, T. Mitsugi, Y. Aono, K. Takahashi, H. Takemoto, J. Biomol. Screening 2002, 7, 267-274.
44. J. Karvinen, P. Hurskainen, S. Gopalakrishnan, D. Burns, U. Warrior, I. Hemmilä, J. Biomol. Screening 2002, 7, 223-231.
45. P. Tawa, J. Tam, R. Cassady, D. W. Nicholson, S. Xanthoudakis, Cell Death Differ. 2001, 8, 30-37.
46. J. P. Waud, A. Bermúdez Fajardo, T. Sudhaharan, A. R. Trimby, J. Jeffery, A. Jones, A. K. Campbell, Biochem. J. 2001, 357, 687-697.
47. Numerous different strategies have been developed for the selective fluorescent labeling of peptides and proteins both in solid-phase and in solution. As examples, see: a) T. Berthelot, J.-C. Talbot, G. Laïn, G. Déleris, L. Latxague, J. Pept. Sci. 2005, 11, 153-160;
48. b) J. Beythien, P. D. White, Tetrahedron Lett. 2005, 46, 101-104;
49. c) M.-P. Brun, L. Bischoff, C. Garbay, Angew. Chem. 2004, 116, 3514-3518;
50. Angew. Chem. Int. Ed. 2004, 43, 3432-3436;
51. d) A. Hamzé, J. Martinez, J.-F. Hernandez, J. Org. Chem. 2004, 69, 8394-8402;
52. e) J. Fernández-Carneado, E. Giralt, Tetrahedron Lett. 2004, 45, 6079-6081;
53. f) N. Koglin, M. Lang, R. Rennert, A. G. Beck-Sickinger, J. Med. Chem. 2003, 46, 4369-4372
54. g) R. G. Kruger, P. Dostal, D. G. McCafferty, Chem. Commun. 2002, 2092-2093;
55. h) N. Tamilarasu, J. Zhang, S. Hwang, T. M. Rana, Bioconjugate Chem. 2001, 12, 135-138.
56. For other examples of FRET probes used for caspase-3 detection, see: a) K. Bullock, D. Piwnica-Worms, J. Med. Chem. 2005, 48, 5404-5407;
57. b) S. Mizukami, K. Kikuchi, T. Higuchi, Y. Urano, T. Mashima, T. Tsuruo, T. Nagano, FEBS Lett. 1999, 453, 356-360.
58. K. Kikuchi, H. Takakusa, T. Nagano, TrAC Trends Anal. Chem. 2004, 24, 407-415.
59. J.-P. Goddard, J.-L. Reymond, Trends Biotechnol. 2004, 22, 363-370.
60. G. B. Fields, R. L. Noble, Int. J. Pept. Protein Res. 1990, 35, 161-214.
61. For a review, see: A. Mishra, R. K. Behera, P. K. Behera, B. K. Mishra, G. B. Behera, Chem. Rev. 2000, 100, 1973-2011.
62. For the synthesis of cyanine dyes Cy3.0 and Cy5.0, see: R. B. Mujumdar, L. A. Ernst, S. R. Mujumdar, C. J. Lewis, A. S. Waggoner, Bioconjugate Chem. 1993, 4, 105-111.
63. See Supporting Information.
64. T. Förster, Discuss. Faraday Soc. 1959, 27, 7-17.
65. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 2nd ed., Kluwer Academic/Plenum, New York, 1999, pp. 367-394.
66. Y. Ishii, T. Yoshida, T. Funatsu, T. Wazawa, T. Yanagida, Chem. Phys. 1999, 247, 163-173.
67. For recent publications about the aspartimide problem in Fmoc-based SPPS, see: a) R. Mergler, F. Dick, B. Sax, P. Weiler, T. Vorherr, J. Pept. Sci. 2003, 9, 36-46
68. b) R. Mergler, F. Dick, B. Sax, C. Stähelin, T. Vorherr, J. Pept. Sci. 2003, 9, 518-526.
69. For a recent publication about the use of DBU in the key step of the synthesis of nucleoside amino acid boranophosphoramidates via an oxathiophospholane approach where no noticeable racemization of amino acid residues was detected, see: P. Li, B. R. Shaw, J. Org. Chem. 2005, 70, 2171-2183.
70. K. Wüthrich, NMR of Proteins and Nucleic Acids, Wiley, New York, 1986.
71. a) B. W. Bycroft, W. C. Chan, S. R. Chhabra, N. D. Hone, J. Chem. Soc. Chem. Commun. 1993, 778-779;
72. b) S. R. Chhabra, B. Hothi, D. J. Evans, P. D. White, B. W. Bycroft, W. C. Chan, Tetrahedron Lett. 1998, 39, 1603-1606;
73. c) J. J. Díaz-Mochón, L. Bialy, M. Bradley, Org. Lett. 2004, 6, 1127-1129;
74. d) L. Bialy, J. J. Díaz-Mochón, E. Specker, L. Keinicke, M. Bradley, Tetrahedron 2005, 61, 8295-8305.
75. A. Aletras, K. Barlos, D. Gatos, S. Koutsogianni, P. Mamos, Int. J. Pept. Protein Res. 1995, 45, 488-496.
76. For recent reviews on synthesis and biological evaluation of glycopeptides, lipidated peptides and proteins, see: a) D. Kadereit, J. Kuhlmann, H. Waldmann, ChemBioChem 2000, 1, 144-169;
77. b) O. Seitz, I. Heinemann, A. Mattes, H. Waldmann, Tetrahedron 2001, 57, 2247-2277;
78. c) H. Waldmann, Bioorg. Med. Chem. 2003, 11, 3045-3051.
79. For recent publications and reviews about the synthesis of bioconjugates by using oxime or semicarbazone ligation chemistries, see: a) T. S. Zatsepin, D. A. Stetsenko, M. J. Gait, T. S. Oretskaya, Bioconjugate Chem. 2005, 16, 471-488;
80. b) T. S. Zatsepin, D. A. Stetsenko, M. J. Gait, T. S. Oretskaya, Tetrahedron Lett. 2005, 46, 3191-3195;
81. c)Y. Sing, O. Renaudet, E. Defrancq, P. Dumy, Org. Lett. 2005, 7, 1359-1362;
82. d) Y. Sing, E. Defrancq, P. Dumy, J. Org. Chem. 2004, 69, 8544-8546;
83. e) L. Bourel-Bonnet, D. Bonnet, F. Malingue, H. Gras-Masse, O. Melnyk, Bioconjugate Chem. 2003, 14, 494-499.
84. For recent publications about the preparation of peptide or oligodeoxynucleotide microarrays by using oxime or semicarbazone ligation chemistry, see: a) C. Olivier, D. Hot, L. Huot, N. Ollivier, O. El-Mahdi, C. Gouyette, T. Huynh-Dinh, H. Gras-Masse, Y. Lemoine, O. Melnyk, Bioconjugate Chem. 2003, 14, 430-439;
85. b) E. Defrancq, A. Hoang, F. Vinet, P. Dumy, Bioorg. Med. Chem. Lett. 2003, 13, 2683-2686;
86. c) C. M. Salisbury, D. J. Maly, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 14868-14870.
87. For thiol- and photolabile protecting groups for aldehydes and ketones, see: a) S. Far, C. Gouyette, O. Melnyk, Tetrahedron 2005, 61, 6138-6142;
88. b) S. Far, O. Melnyk, Tetrahedron Lett. 2004, 45, 7163-7165;
89. c) S. Kantevari, Ch. V. Narasimhaji, H. Mereyala, Tetrahedron 2005, 61, 5849-5854;
90. d) A. Blanc, C. G. Bochet, J. Org. Chem. 2003, 68, 1138-1141;
91. e) M. Lu, O. D. Fedoryak, B. R. Moister, T. M. Dore, Org. Lett. 2003, 5, 2119-2122.
92. H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 1997, 62, 7512-7515.
93. M. Piotto, V. Saudek, V. Sklenar, J. Biomol. NMR 1992, 2, 661-665.
94. E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, Anal. Biochem. 1970, 34, 595-598.
95. W. Bannwarth, R. Knorr, Tetrahedron Lett. 1991, 32, 1157-1160.