N-terminal protein modification using simple aminoacyl transferase substrates

Journal of the American Chemical Society

Volumn 133, Issue 38, 2011, Pages 15139-15147

  Wagner, Anne M ^a   Fegley, Mark W ^a   Warner, John B ^a   Grindley, Christina L J ^a   Marotta, Nicholas P ^a,b   Petersson, E James ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOACYL; ENZYMATIC ACTIVITIES; N-TERMINALS; POTENTIAL SUBSTRATE; PROTEIN FUNCTIONS; PROTEIN MODIFICATIONS; PROTEIN STRUCTURES; SUBSTRATE LIMITATION; SYNTHETASES;

AMINO ACIDS; ESCHERICHIA COLI; OLIGONUCLEOTIDES; PROTEINS; SYNTHESIS (CHEMICAL);

SUBSTRATES;

ADENOSINE; AMINOACYL TRANSFER RNA; AMINOACYL TRANSFERRNA TRANSFERASE; AMINOACYLTRANSFERASE; OLIGONUCLEOTIDE; PHENYLALANINE; SYNTHETASE; TRANSFER RNA; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL REACTION; ENZYME ACTIVITY; ESCHERICHIA COLI; NONHUMAN; PROTEIN FUNCTION; PROTEIN MODIFICATION; PROTEIN STRUCTURE; SYNTHESIS;

ADENOSINE; AMINOACYLTRANSFERASES; BIOCATALYSIS; CASEINS; ESCHERICHIA COLI; MOLECULAR STRUCTURE; SUBSTRATE SPECIFICITY;

EID: 80053069963     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2055098     Document Type: Article

References (89)

1. Wu, P. G.; Brand, L. In Fluorescence Spectroscopy; Academic Press: San Diego, CA, 1997; Vol. 278, pp 321-330.
2. Harris, J. M.; Chess, R. B. Nat. Rev. Drug Discovery 2003, 2, 214-221
3. Wang, L.; Schultz, P. G. Angew. Chem., Int. Ed. 2005, 44, 34-66
4. Basle, E.; Joubert, N.; Pucheault, M. Chem. Biol. 2010, 17, 213-227
5. Canalle, L. A.; Lowik, D.; van Hest, J. C. M. Chem. Soc. Rev. 2010, 39, 329-353
6. Alouani, S.; Gaertner, H. F.; Mermod, J. J.; Power, C. A.; Bacon, K. B.; Wells, T. N. C.; Proudfoot, A. E. I. Eur. J. Biochem. 1995, 227, 328-334
7. Kinstler, O. B.; Brems, D. N.; Lauren, S. L.; Paige, A. G.; Hamburger, J. B.; Treuheit, M. J. Pharm. Res. 1996, 13, 996-1002
8. Gale, T. F.; Gorlitzer, J.; O'Brien, S. W.; Williams, D. H. J. Chem. Soc., Perkin 1 1999, 2267-2270
9. Ramachandiran, V.; Willms, C.; Kramer, G.; Hardesty, B. J. Biol. Chem. 2000, 275, 1781-1786
10. Jones, D. S.; Cockerill, K. A.; Gamino, C. A.; Hammaker, J. R.; Hayag, M. S.; Iverson, G. M.; Linnik, M. D.; McNeeley, P. A.; Tedder, M. E.; Ton-Nu, H. T.; Victoria, E. J. Bioconj. Chem. 2001, 12, 1012-1020
11. Kinstler, O.; Molineux, G.; Treuheit, M.; Ladd, D.; Gegg, C. Adv. Drug Delivery Rev. 2002, 54, 477-485
12. Chelius, D.; Shaler, T. A. Bioconj. Chem. 2003, 14, 205-211
13. Arduini, R. M. Protein Exp. Purification 2004, 34, 229-242
14. Mamaev, S.; Olejnik, J.; Olejnik, E. K.; Rothschild, K. J. Anal. Biochem. 2004, 326, 25-32
15. Baker, D. P. Bioconj. Chem. 2006, 17, 179-188
16. Scheck, R. A.; Francis, M. B. ACS Chem. Biol. 2007, 2, 247-251
17. Merkel, L.; Beckmann, H. S. G.; Wittmann, V.; Budisa, N. ChemBioChem 2008, 9, 1220-1224
18. Sharon, J. L.; Puleo, D. A. Biomaterials 2008, 29, 3137-3142
19. Ebhardt, H. A.; Xu, Z. Z.; Fung, A. W.; Fahlman, R. P. Anal. Chem. 2009, 81, 1937-1943
20. Gao, W. P.; Liu, W. G.; Mackay, J. A.; Zalutsky, M. R.; Toone, E. J.; Chilkoti, A. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 15231-15236
21. Sayers, C. T.; Mantovani, G.; Ryan, S. M.; Randev, R. K.; Keiper, O.; Leszczyszyn, O. I.; Blindauer, C.; Brayden, D. J.; Haddleton, D. M. Soft Matter 2009, 5, 3038-3046
22. Xiao, J. P.; Tolbert, T. J. Org. Lett. 2009, 11, 4144-4147
23. Jia, J.; Chen, W.; Ma, H. M.; Wang, K.; Zhao, C. A. Mol. Biosyst. 2010, 6, 1829-1833
24. Wang, J.; Hu, T.; Liu, Y. D.; Zhang, G. F.; Ma, G. H.; Su, Z. G. Anal. Biochem. 2010, 412, 114-116
25. Wildes, D.; Wells, J. A. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 4561-4566
26. Wu, J. J.; Peng, H. T.; Shek, P. N. J. App. Poly. Sci. 2010, 118, 3269-3273
27. Goldberg, J. M.; Batjargal, S.; Petersson, E. J. J. Am. Chem. Soc. 2010, 132, 14718-14720
28. Dixon, H. B. F.; Weitkamp, L. R. Biochem. J. 1962, 84, 462-468
29. Dixon, H. B. F. Biochem. J. 1964, 92, 661-666
30. Geoghegan, K. F.; Ybarra, D. M.; Feeney, R. E. Biochemistry 1979, 18, 5392-5399
31. Dixon, H. B. F. J. Protein Chem. 1984, 3, 99-108
32. Acharya, A. S.; Manjula, B. N. Biochemistry 1987, 26, 3524-3530
33. Qasmi, D.; Rene, L.; Badet, B. Tetrahedron Lett. 1994, 35, 4343-4344
34. Li, X. F.; Zhang, L. S.; Hall, S. E.; Tam, J. P. Tetrahedron Lett. 2000, 41, 4069-4073
35. Gilmore, J. M.; Scheck, R. A.; Esser-Kahn, A. P.; Joshi, N. S.; Francis, M. B. Angew. Chem., Int. Ed. 2006, 45, 5307-5311
36. Scheck, R. A.; Dedeo, M. T.; Lavarone, A. T.; Francis, M. B. J. Am. Chem. Soc. 2008, 130, 11762-11770
37. Witus, L. S.; Moore, T.; Thuronyi, B. W.; Esser-Kahn, A. P.; Scheck, R. A.; Iayarone, A. T.; Francis, M. B. J. Am. Chem. Soc. 2010, 132, 16812-16817
38. Kuhl, P.; Konnecke, A.; Doring, G.; Daumer, H.; Jakubke, H. D. Tetrahedron Lett. 1980, 21, 893-896
39. Jakubke, H. D.; Kuhl, P.; Konnecke, A. Angew. Chem., Int. Ed. 1985, 24, 85-93
40. Schellenberger, V.; Jakubke, H. D. Angew. Chem., Int. Ed. 1991, 30, 1437-1449
41. Chang, T. K.; Jackson, D. Y.; Burnier, J. P.; Wells, J. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 12544-12548
42. Jackson, D. Y.; Burnier, J.; Quan, C.; Stanley, M.; Tom, J.; Wells, J. A. Science 1994, 266, 243-247
43. Bordusa, F.; Ullmann, D.; Elsner, C.; Jakubke, H. D. Angew. Chem., Int. Ed. 1997, 36, 2473-2475
44. Braisted, A. C.; Judice, J. K.; Wells, J. A. In Solid-Phase Peptide Synthesis; Academic Press: San Diego, CA, 1997; Vol. 289, pp 298-313.
45. Atwell, S.; Wells, J. A. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9497-9502
46. Bordusa, F. Chem. Rev. 2002, 102, 4817-4867
47. Tolbert, T. J.; Wong, C. H. Angew. Chem., Int. Ed. 2002, 41, 2171-2174
48. Muir, T. W. Annu. Rev. Biochem. 2003, 72, 249-289
49. Wehofsky, N.; Koglin, N.; Thust, S.; Bordusa, F. J. Am. Chem. Soc. 2003, 125, 6126-6133
50. Gentle, I. E.; De Souza, D. P.; Baca, M. Bioconj. Chem. 2004, 15, 658-663
51. Yoshihara, H. A. I.; Mahrus, S.; Wells, J. A. Bioorg. Med. Chem. Lett. 2008, 18, 6000-6003
52. Mazmanian, S. K.; Liu, G.; Hung, T. T.; Schneewind, O. Science 1999, 285, 760-763
53. Mao, H. Y.; Hart, S. A.; Schink, A.; Pollok, B. A. J. Am. Chem. Soc. 2004, 126, 2670-2671
54. Tanaka, T.; Kamiya, N.; Nagamune, T. FEBS Lett. 2005, 579, 2092-2096
55. Popp, M. W.; Antos, J. M.; Grotenbreg, G. M.; Spooner, E.; Ploegh, H. L. Nat. Chem. Biol. 2007, 3, 707-708
56. Fontana, A.; Spolaore, B.; Mero, A.; Veronese, F. M. Adv. Drug Delivery Rev. 2008, 60, 13-28
57. Heal, W. P.; Wickramasinghe, S. R.; Leatherbarrow, R. J.; Tate, E. W. Org. Biomol. Chem. 2008, 6, 2308-2315
58. Tsukiji, S.; Nagamune, T. ChemBioChem 2009, 10, 787-798
59. Nelson, J. W.; Chamessian, A. G.; McEnaney, P. J.; Murelli, R. P.; Kazmiercak, B. I.; Spiegel, D. A. ACS Chem. Biol. 2010, 5, 1147-1155
60. Lahoud, G.; Hou, Y. M. Nat. Chem. Biol. 2010, 6, 795-796
61. Kaji, A.; Novelli, G. D.; Kaji, H. Biochem. Biophys. Res. Commun. 1963, 10, 406-409
62. Suto, K.; Shimizu, Y.; Watanabe, K.; Ueda, T.; Fukai, S.; Nureki, O.; Tomita, K. EMBO J. 2006, 25, 5942-5950
63. Watanabe, K.; Toh, Y.; Suto, K.; Shimizu, Y.; Oka, N.; Wada, T.; Tomita, K. Nature 2007, 449, 867-871
64. Mogk, A.; Schmidt, R.; Bukau, B. Trends Cell Biol. 2007, 17, 165-172
65. Tobias, J. W.; Shrader, T. E.; Rocap, G.; Varshavsky, A. Science 1991, 254, 1374-1377
66. Varshavsky, A. Nat. Struct. Mol. Biol. 2008, 15, 1238-1240
67. Schuenemann, V. J.; Kralik, S. M.; Albrecht, R.; Spall, S. K.; Truscott, K. N.; Dougan, D. A.; Zeth, K. EMBO Rep. 2009, 10, 508-514
68. Kaji, A.; Kaji, H.; Novelli, G. D. J. Biol. Chem. 1965, 240, 1185-1191
69. Kaji, A.; Kaji, H.; Novelli, G. D. J. Biol. Chem. 1965, 240, 1192-1197
70. Leibowitz, M. J.; Soffer, R. L. Biochem. Biophys. Res. Commun. 1969, 36, 47-53
71. Leibowitz, M. J. J. Biol. Chem. 1971, 246, 5207-5212
72. Taki, M.; Kuno, A.; Matoba, S.; Kobayashi, Y.; Futami, J.; Murakami, H.; Suga, H.; Taira, K.; Hasegawa, T.; Sisido, M. ChemBioChem 2006, 7, 1676-1679
73. Taki, M.; Sisido, M. Biopolymers 2007, 88, 263-271
74. Taki, M.; Kuroiwa, H.; Sisido, M. ChemBioChem 2008, 9, 719-722
75. Ebisu, K.; Tateno, H.; Kuroiwa, H.; Kawakami, K.; Ikeuchi, M.; Hirabayashi, J.; Sisido, M.; Taki, M. ChemBioChem 2009, 10, 2460-2464
76. Abramochkin, G.; Shrader, T. E. J. Biol. Chem. 1995, 270, 20621-20628
77. Abramochkin, G.; Shrader, T. E. J. Biol. Chem. 1996, 271, 22901-22907
78. Connor, R. E.; Piatkov, K.; Varshavsky, A.; Tirrell, D. A. ChemBioChem 2008, 9, 366-369
79. Fersht, A. Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding, 3 rd ed.; W. H. Freeman: New York, 1998.
80. Mercier, J. C.; Grosclau, F.; Ribadeau, B. Eur. J. Biochem. 1971, 23, 41-51
81. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
82. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193
83. Huisgen, R. Pure App. Chem. 1989, 61, 613-628
84. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015
85. Hackenberger, C. P. R.; Schwarzer, D. Angew. Chem., Int. Ed. 2008, 47, 10030-10074
86. Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974-6998
87. Carrico, I. S. Chem. Soc. Rev. 2008, 37, 1423-1431
88. Ogilvie, K. K.; Letsinge, R. I. J. Org. Chem. 1967, 32, 2365-2366
89. Ellman, J.; Mendel, D.; Anthonycahill, S.; Noren, C. J.; Schultz, P. G. Methods Enzymol. 1991, 202, 301-336