Genetic encoding of caged cysteine and caged homocysteine in bacterial and mammalian cells

ChemBioChem

Volumn 15, Issue 12, 2014, Pages 1793-1799

  Uprety, Rajendra ^a   Luo, Ji ^b   Liu, Jihe ^b   Naro, Yuta ^b   Samanta, Subhas ^b   Deiters, Alexander ^a,b  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

amino acids; caged compounds; cysteine; gene technology; homocysteine; protein modifications

Indexed keywords

AMINO ACID TRANSFER RNA LIGASE; CYSTEINE; HOMOCYSTEINE; RENILLA LUCIFERIN 2 MONOOXYGENASE; TRANSFER RNA;

ANIMAL CELL; ARTICLE; BACTERIAL CELL; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SYNTHESIS; GENETIC CODE; HUMAN; HUMAN CELL; MAMMAL CELL; MASS SPECTROMETRY; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; RADIATION EXPOSURE; ULTRAVIOLET RADIATION; WESTERN BLOTTING; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; ESCHERICHIA COLI; GENETICS; HEK293 CELL LINE; METABOLISM; SYNTHESIS;

CELLS, CULTURED; CYSTEINE; ESCHERICHIA COLI; GENETIC CODE; HEK293 CELLS; HOMOCYSTEINE; HUMANS; LUCIFERASES, RENILLA; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 84906061962     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201400073     Document Type: Article

References (91)

1. N. J. Pace, E. Weerapana, ACS Chem. Biol. 2013, 8, 283-296.
2. Y. Kim, S. O. Ho, N. R. Gassman, Y. Korlann, E. V. Landorf, F. R. Collart, S. Weiss, Bioconjugate Chem. 2008, 19, 786-791
3. E. Baslé, N. Joubert, M. Pucheault, Chem. Biol. 2010, 17, 213-227
4. H. Antelmann, J. D. Helmann, Antioxid. Redox Signaling 2011, 14, 1049-1063
5. K. G. Reddie, K. S. Carroll, Curr. Opin. Chem. Biol. 2008, 12, 746-754.
6. L. Spasser, A. Brik, Angew. Chem. Int. Ed. 2012, 51, 6840-6862
7. Angew. Chem. 2012, 124, 6946-6969
8. T. Tasaki, Y. T. Kwon, Trends Biochem. Sci. 2007, 32, 520-528.
9. M. Lamkanfi, N. Festjens, W. Declercq, T. Vanden Berghe, P. Vandenabeele, Cell Death Differ. 2007, 14, 44-55
10. S. J. Riedl, Y. Shi, Nat. Rev. Mol. Cell Biol. 2004, 5, 897-907.
11. M. Kemp, Y. M. Go, D. P. Jones, Free Radical Biol. Med. 2008, 44, 921-937.
12. L. E. Netto, M. A. de Oliveira, G. Monteiro, A. P. Demasi, J. R. Cussiol, K. F. Discola, M. Demasi, G. M. Silva, S. V. Alves, V. G. Faria, B. B. Horta, Comp. Biochem. Physiol. C 2007, 146, 180-193
13. L. E. Shao, T. Tanaka, R. Gribi, J. Yu, Ann. N. Y. Acad. Sci. 2002, 962, 140-150
14. D. P. Jones, Am. J. Physiol. Cell Physiol. 2008, 295, C 849-868
15. R. S. Balaban, S. Nemoto, T. Finkel, Cell 2005, 120, 483-495
16. T. Finkel, Nat. Rev. Mol. Cell Biol. 2005, 6, 971-976.
17. A. Delaunay, D. Pflieger, M. B. Barrault, J. Vinh, M. B. Toledano, Cell 2002, 111, 471-481
18. Y. Collins, E. T. Chouchani, A. M. James, K. E. Menger, H. M. Cocheme, M. P. Murphy, J. Cell Sci. 2012, 125, 801-806.
19. G. Bastin, K. Singh, K. Dissanayake, A. S. Mighiu, A. Nurmohamed, S. P. Heximer, J. Biol. Chem. 2012, 287, 28966-28974
20. J. Greaves, L. H. Chamberlain, J. Cell Biol. 2007, 176, 249-254
21. J. E. Smotrys, M. E. Linder, Annu. Rev. Biochem. 2004, 73, 559-587
22. A. Higdon, A. R. Diers, J. Y. Oh, A. Landar, V. M. Darley-Usmar, Biochem. J. 2012, 442, 453-464.
23. M. Lindahl, A. Mata-Cabana, T. Kieselbach, Antioxid. Redox Signaling 2011, 14, 2581-2642.
24. N. M. Giles, G. I. Giles, C. Jacob, Biochem. Biophys. Res. Commun. 2003, 300, 1-4.
25. D. Fass, Annu. Rev. Biophys. Bioeng. 2012, 41, 63-79.
26. A. S. Wierzbicki, Diab. Vasc. Dis. Res. 2007, 4, 143-150.
27. S. Seshadri, A. Beiser, J. Selhub, P. F. Jacques, I. H. Rosenberg, R. B. D'Agostino, P. W. F. Wilson, P. A. Wolf, New Engl. J. Med. 2002, 346, 476-483.
28. H. Jakubowski, J. Biol. Chem. 1997, 272, 1935-1942.
29. A. V. Glushchenko, D. W. Jacobsen, Antioxid. Redox Signaling 2007, 9, 1883-1898.
30. H. Jakubowski, J. Nutr. 2006, 136, 1741S-1749S.
31. P. Paoli, F. Sbrana, B. Tiribilli, A. Caselli, B. Pantera, P. Cirri, A. De Donatis, L. Formigli, D. Nosi, G. Manao, G. Camici, G. Ramponi, J. Mol. Biol. 2010, 400, 889-907.
32. A. Undas, J. Perla, M. Lacinski, W. Trzeciak, R. Kazmierski, H. Jakubowski, Stroke 2004, 35, 1299-1304.
33. H. M. Lee, D. R. Larson, D. S. Lawrence, ACS Chem. Biol. 2009, 4, 409-427
34. A. Deiters, ChemBioChem 2010, 11, 47-53
35. C. W. Riggsbee, A. Deiters, Trends Biotechnol. 2010, 28, 468-475
36. L. Gardner, A. Deiters, Curr. Opin. Chem. Biol. 2012, 16, 292-299
37. C. Brieke, F. Rohrbach, A. Gottschalk, G. Mayer, A. Heckel, Angew. Chem. Int. Ed. 2012, 51, 8446-8476
38. Angew. Chem. 2012, 124, 8572-8604.
39. A. Deiters, D. Groff, Y. Ryu, J. Xie, P. G. Schultz, Angew. Chem. Int. Ed. 2006, 45, 2728-2731
40. Angew. Chem. 2006, 118, 2794-2797
41. A. Gautier, D. P. Nguyen, H. Lusic, W. An, A. Deiters, J. W. Chin, J. Am. Chem. Soc. 2010, 132, 4086-4088
42. Y.-S. Wang, B. Wu, Z. Wang, Y. Huang, W. Wan, W. K. Russell, P.-J. Pai, Y. N. Moe, D. H. Russell, W. R. Liu, Mol. BioSyst. 2010, 6, 1557-1560
43. D. Groff, P. R. Chen, F. B. Peters, P. G. Schultz, ChemBioChem 2010, 11, 1066-1068.
44. W. F. Edwards, D. D. Young, A. Deiters, ACS Chem. Biol. 2009, 4, 441-445
45. C. Chou, D. D. Young, A. Deiters, Angew. Chem. Int. Ed. 2009, 48, 5950-5953
46. Angew. Chem. 2009, 121, 6064-6067
47. C. Chou, D. D. Young, A. Deiters, ChemBioChem 2010, 11, 972-977
48. C. Chou, A. Deiters, Angew. Chem. Int. Ed. 2011, 50, 6839-6842
49. Angew. Chem. 2011, 123, 6971-6974
50. A. Gautier, A. Deiters, J. W. Chin, J. Am. Chem. Soc. 2011, 133, 2124-2127
51. E. Arbely, J. Torres-Kolbus, A. Deiters, J. W. Chin, J. Am. Chem. Soc. 2012, 134, 11912-11915
52. J. Hemphill, C. Chou, J. W. Chin, A. Deiters, J. Am. Chem. Soc. 2013, 135, 13433-13439.
53. N. Wu, A. Deiters, T. A. Cropp, D. King, P. G. Schultz, J. Am. Chem. Soc. 2004, 126, 14306-14307
54. E. A. Lemke, D. Summerer, B. H. Geierstanger, S. M. Brittain, P. G. Schultz, Nat. Chem. Biol. 2007, 3, 769-772
55. J.-Y. Kang, D. Kawaguchi, I. Coin, Z. Xiang, D. D. M. O'Leary, P. A. Slesinger, L. Wang, Neuron 2013, 80, 358-370
56. D. P. Nguyen, M. Mahesh, S. J. Elsässer, S. M. Hancock, C. Uttamapinant, J. W. Chin, J. Am. Chem. Soc. 2014, 136, 2240-2243.
57. W. Wan, J. M. Tharp, W. R. Liu, Biochim. Biophys. Acta Proteins Proteomics 2014, 1844, 1059-1070
58. H. Neumann, S. Y. Peak-Chew, J. W. Chin, Nat. Chem. Biol. 2008, 4, 232-234
59. T. Yanagisawa, R. Ishii, R. Fukunaga, T. Kobayashi, K. Sakamoto, S. Yokoyama, Chem. Biol. 2008, 15, 1187-1197
60. P. R. Chen, D. Groff, J. Guo, W. Ou, S. Cellitti, B. H. Geierstanger, P. G. Schultz, Angew. Chem. Int. Ed. 2009, 48, 4052-4055
61. Angew. Chem. 2009, 121, 4112-4115
62. D. P. Nguyen, H. Lusic, H. Neumann, P. B. Kapadnis, A. Deiters, J. W. Chin, J. Am. Chem. Soc. 2009, 131, 8720-8721
63. C. J. Chou, R. Uprety, L. Davis, J. W. Chin, A. Deiters, Chem. Sci. 2011, 2, 480-483
64. C. H. Kim, M. Kang, H. J. Kim, A. Chatterjee, P. G. Schultz, Angew. Chem. Int. Ed. 2012, 51, 7246-7249
65. Angew. Chem. 2012, 124, 7358-7361
66. K. Lang, L. Davis, J. Torres-Kolbus, C. Chou, A. Deiters, J. W. Chin, Nat. Chem. 2012, 4, 298-304.
67. E. Anderson, T. Brown, D. Picken, Nucleosides Nucleotides Nucleic Acids 2003, 22, 1403-1406.
68. C. Z. Ding, R. B. Silverman, Synth. Commun. 1993, 23, 1467-1471.
69. I. S. Weitz, M. Pellegrini, D. F. Mierke, M. Chorev, J. Org. Chem. 1997, 62, 2527-2534
70. C. E. McInnis, H. E. Blackwell, Bioorg. Med. Chem. 2011, 19, 4820-4828.
71. N. Eswar, B. Webb, M. A. Marti-Renom, M. S. Madhusudhan, D. Eramian, M. Y. Shen, U. Pieper, A. Sali, Curr. Protoc. Bioinf. 2006, Unit 5 6.
72. T. A. Darden, D. A. Case, T. E. Cheatham III, C. L. Simmerling, J. Wang, R. E. Duke, R. Luo, R. C. Walker, W. Zhang, K. M. Merz, B. Roberts, S. Hayik, A. Roitberg, G. Seabra, J. Swails, A. W. Goetz, I. Kolossváry, K. F. Wong, F. Paesani, J. Vanicek, R. M. Wolf, J. Liu, X. Wu, S. R. Brozell, T. Steinbrecher, H. Gohlke, Q. Cai, X. Ye, J. Wang, M.-J. Hsieh, G. Cui, D. R. Roe, D. H. Mathews, M. G. Seetin, R. Salomon-Ferrer, C. Sagui, V. Babin, T. Luchko, S. Gusarov, A. Kovalenko, P. A. Kollman in AMBER 12, University of California, San Francisco, San Francisco, CA, 2012.
73. O. Trott, A. J. Olson, J. Comput. Chem. 2010, 31, 455-461.
74. J. M. Kavran, S. Gundllapalli, P. O'Donoghue, M. Englert, D. Soll, T. A. Steitz, Proc. Natl. Acad. Sci. USA 2007, 104, 11268-11273
75. J. K. Takimoto, N. Dellas, J. P. Noel, L. Wang, ACS Chem. Biol. 2011, 6, 733-743.
76. S. Schneider, M. J. Gattner, M. Vrabel, V. Flugel, V. Lopez-Carrillo, S. Prill, T. Carell, ChemBioChem 2013, 14, 2114-2118
77. T. Yanagisawa, T. Sumida, R. Ishii, S. Yokoyama, Acta Crystallogr. Sect. D 2013, 69, 5-15
78. T. Yanagisawa, R. Ishii, R. Fukunaga, T. Kobayashi, K. Sakamoto, S. Yokoyama, J. Mol. Biol. 2008, 378, 634-652.
79. S. Bhaumik, S. S. Gambhir, Proc. Natl. Acad. Sci. USA 2002, 99, 377-382.
80. J. Zhao, S. Lin, Y. Huang, J. Zhao, P. R. Chen, J. Am. Chem. Soc. 2013, 135, 7410-7413.
81. A. M. Loening, T. D. Fenn, S. S. Gambhir, J. Mol. Biol. 2007, 374, 1017-1028
82. J. Woo, M. H. Howell, A. G. von Arnim, Protein Sci. 2008, 17, 725-735
83. A. M. Loening, T. D. Fenn, A. M. Wu, S. S. Gambhir, Protein Eng. Des. Sel. 2006, 19, 391-400.
84. Y. S. Wang, X. Fang, A. L. Wallace, B. Wu, W. R. Liu, J. Am. Chem. Soc. 2012, 134, 2950-2953
85. S. Greiss, J. W. Chin, J. Am. Chem. Soc. 2011, 133, 14196-14199.
86. D. Schwarzer, C. Ludwig, I. V. Thiel, H. D. Mootz, Biochemistry 2012, 51, 233-242.
87. O. Allnér, L. Nilsson, A. Villa, J. Chem. Theory Comput. 2012, 8, 1493-1502
88. K. L. Meagher, L. T. Redman, H. A. Carlson, J. Comput. Chem. 2003, 24, 1016-1025.
89. K. Lindorff-Larsen, S. Piana, K. Palmo, P. Maragakis, J. L. Klepeis, R. O. Dror, D. E. Shaw, Proteins Struct. Funct. Bioinf. 2010, 78, 1950-1958.
90. G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comput. Chem. 2009, 30, 2785-2791.
91. T. A. Halgren, J. Comput. Chem. 1996, 17, 616-641.