Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles

Biopolymers

Volumn 104, Issue 6, 2015, Pages 663-673

  Qian, Wen Jian ^a   Park, Jung Eun ^b   Grant, Robert ^c   Lai, Christopher C ^a   Kelley, James A ^a   Yaffe, Michael B ^c   Lee, Kyung S ^b   Burke, Terrence R ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

cationic dialkyl histidine; crystal structure; peptide macrocycles, phosphopeptides; Plk1; polo kinase; polo box domain

Indexed keywords

ALKYLATION; BIOMIMETICS; CRYSTAL STRUCTURE; PEPTIDES;

CATIONIC DIALKYL HISTIDINE; MACROCYCLES; PLK1; POLO KINASE; POLO-BOX DOMAIN;

AMINO ACIDS;

HISTIDINE; HISTIDINE N; IMIDAZOLE DERIVATIVE; IMIDAZOLIUM; MACROCYCLIC COMPOUND; PHOSPHOAMINO ACID; PHOSPHOPEPTIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

ALKYLATION; CRYSTALLOGRAPHY, X-RAY; HISTIDINE; IMIDAZOLES; MACROCYCLIC COMPOUNDS; PHOSPHOPEPTIDES;

EID: 84962210045     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.22698     Document Type: Article

References (40)

1. Qian, W.-J.,;, Park, J.-E.,;, Lim, D.,;, Lai, C. C.,;, Kelley, J. A.,;, Park, S.-Y.,;, Lee, K. W.,;, Yaffe, M. B.,;, Lee, K. S.,;, Burke, T. R., Biopolym Pept Sci 2014, 102, 444-455.
2. Qian, W.-J.,;, Burke, T. R., Jr., Org Biomol Chem 2015, 13, 4221-4225.
3. Yun, S.-M.,;, Moulaei, T.,;, Lim, D.,;, Bang, J. K.,;, Park, J.-E.,;, Shenoy, S. R.,;, Liu, F.,;, Kang, Y. H.,;, Liao, C.,;, Soung, N.-K.,;, Lee, S.,;, Yoon, D.-Y.,;, Lim, Y.,;, Lee, D.-H.,;, Otaka, A.,;, Appella, E.,;, McMahon, J. B.,;, Nicklaus, M. C.,;, Burke, T. R., Jr.,;, Yaffe, M. B.,;, Wlodawer, A.,;, Lee, K. S., Nat Struct Mol Biol 2009, 16, 876-882.
4. Liu, F.,;, Park, J.-E.,;, Qian, W.-J.,;, Lim, D.,;, Graber, M.,;, Berg, T.,;, Yaffe, M. B.,;, Lee, K. S.,;, Burke, T. R., Jr., Nat Chem Biol 2011, 7, 595-601.
5. Allentoff, A. J.,;, Mandiyan, S.,;, Liang, H.,;, Yuryev, A.,;, Vlattas, I.,;, Duelfer, T.,;, Sytwu, I.-I.,;, Wennogle, L. P., Cell Biochem Biophys 1999, 31, 129-140.
6. Davies, J. S., J Pept Sci 2003, 9, 471-501.
7. Jiang, S.,;, Li, Z.,;, Ding, K.,;, Roller, P. P., Curr Org Chem 2008, 12, 1502-1542.
8. White, C. J.,;, Yudin, A. K., Nat Chem 2011, 3, 509-524.
9. Dharanipragada, R., Future Med Chem 2013, 5, 831-849.
10. Murugan, R. N.,;, Park, J.-E.,;, Lim, D.,;, Ahn, M.,;, Cheong, C.,;, Kwon, T.,;, Nam, K.-Y.,;, Choi, S. H.,;, Kim, B. Y.,;, Yoon, D.-Y.,;, Yaffe, M. B.,;, Yu, D.-Y.,;, Lee, K. S.,;, Bang, J. K., Bioorg Med Chem 2013, 21, 2623-2634.
11. Qian, W.,;, Liu, F.,;, Burke, T. R., Jr., J Org Chem 2011, 76, 8885-8890.
12. Blackwell, H. E.,;, Sadowsky, J. D.,;, Howard, R. J.,;, Sampson, J. N.,;, Chao, J. A.,;, Steinmetz, W. E.,;, O'Leary, D. J.,;, Grubbs, R. H., J Org Chem 2001, 66, 5291-5302.
13. Liu, F.,;, Giubellino, A.,;, Simister, P. C.,;, Qian, W.,;, Giano, M. C.,;, Feller, S. M.,;, Bottaro, D. P.,;, Burke, T. R., Jr., Biopolymers 2011, 96, 780-788.
14. Chapman, R. N.,;, Arora, P. S., Org Lett 2006, 8, 5825-5828.
15. Robinson, A. J.,;, Elaridi, J.,;, Van Lierop, B. J.,;, Mujcinovic, S.,;, Jackson, W. R., J Pept Sci 2007, 13, 280-285.
16. Robinson, A. J.,;, van Lierop, B. J.,;, Garland, R. D.,;, Teoh, E.,;, Elaridi, J.,;, Illesinghe, J. P.,;, Jackson, W. R., Chem. Commun. 2009, 4293-4295.
17. García-Aranda, M. I.,;, Marrero, P.,;, Gautier, B.,;, Martín-Martínez, M.,;, Inguimbert, N.,;, Vidal, M.,;, García-López, M. T.,;, Jiménez, M. A.,;, González-Muñiz, R.,;, Vega, M. J. P., Bioorg Med Chem 2011, 19, 1978-1986.
18. Mulder, M. P. C.,;, Kruijtzer, J. A. W.,;, Breukink, E. J.,;, Kemmink, J.,;, Pieters, R. J.,;, Liskamp, R. M. J., Bioorg Med Chem 2011, 19, 6505-6517.
19. Heapy, A. M.,;, Williams, G. M.,;, Fraser, J. D.,;, Brimble, M. A., Org Lett 2012, 14, 878-881.
20. Scholl, M.,;, Ding, S.,;, Lee, C. W.,;, Grubbs, R. H., Org Lett 1999, 1, 953-956.
21. Garber, S. B.,;, Kingsbury, J. S.,;, Gray, B. L.,;, Hoveyda, A. H., J Am Chem Soc 2000, 122, 8168-8179.
22. Michalak, M.,;, Wicha, J., Org Biomol Chem 2011, 9, 3439-3446.
23. Stoianova, D. S.,;, Hanson, P. R., Org Lett 2000, 2, 1769-1772.
24. Heckrodt, T. J.,;, Singh, R., Synth Commun 2012, 42, 2854-2865.
25. Maysuya, Y.,;, Takayanagi, S.-I.,;, Nemoto, H., Chem-Eur J 2008, 14, 5275-5281.
26. Buszek, K. R.,;, Brown, N., J Org Chem 2007, 72, 3125-3128.
27. García-Aranda, M. I.,;, González-Muñiz, R.,;, García-López, M. T.,;, Pérez de Vega, M. J., Eur J Org Chem 2009, 2009, 4149-4157.
28. Palumbo, A. M.,;, Tepe, J. J.,;, Reid, G. E., J Proteome Res 2008, 7, 771-779.
29. Boersema, P. J.,;, Mohammed, S.,;, Heck, A. J. R., J Mass Spectrom 2009, 44, 861-878.
30. Bythell, B. J.,;, Suhai, S.,;, Somogyi, Á.,;, Paizs, B., J Am Chem Soc 2009, 131, 14057-14065.
31. Kang, Y. H.,;, Park, J.-E.,;, Yu, L.-R.,;, Soung, N.-K.,;, Yun, S.-M.,;, Bang, J. K.,;, Seong, Y.-S.,;, Yu, H.,;, Garfield, S.,;, Veenstra, T. D.,;, Lee, K. S., Mol Cell 2006, 24, 409-422.
32. MolSoft LLC, ICM Pro Software v3.8-0/MacOSX, MolSoft LLC, La Jolla, CA.
33. Abagyan, R.,;, Orry, A.,;, Raush, E.,;, Totrov, M., ICM-Chemist-Pro User Guide v38. Available at: Http://www.molsoft.com/chemistpro/
34. Elia, A. E.,;, Rellos, P.,;, Haire, L. F.,;, Chao, J. W.,;, Ivins, F. J.,;, Hoepker, K.,;, Mohammad, D.,;, Cantley, L. C.,;, Smerdon, S. J.,;, Yaffe, M. B., Cell 2003, 115, 83-95.
35. Murugan, R. N.,;, Ahn, M.,;, Lee, W. C.,;, Kim, H.-Y.,;, Song, J. H.,;, Cheong, C.,;, Hwang, E.,;, Seo, J.-H.,;, Shin, S. Y.,;, Choi, S. H.,;, Park, J.-E.,;, Bang, J. K., PLoS One 2013, 8, e80043.
36. Peters, C.,;, Bacher, M.,;, Buenemann, C. L.,;, Kricek, F.,;, Rondeau, J.-M.,;, Weigand, K., ChemBioChem 2007, 8, 1785-1789.
37. Otwinowski, Z.,;, Minor, W., In Macromolecular Crystallography, Part A;, Carter, C. W., Jr.,;, Sweet, R. M., Eds.; Academic Press: New York, NY, 1997; pp 307-326.
38. McCoy, A. J.,;, Grosse-Kunstleve, R. W.,;, Adams, P. D.,;, Winn, M. D.,;, Storoni, L. C.,;, Read, R. J., J Appl Cryst 2007, 40, 658-674.
39. Emsley, P.,;, Cowtan, K., Acta Crystallogr D Biol Crystallogr 2004, 60, 2126-2132.
40. Adams, P. D.,;, Afonine, P. V.,;, Bunkoczi, G.,;, Chen, V. B.,;, Davis, I. W.,;, Echols, N.,;, Headd, J. J.,;, Hung, L. W.,;, Kapral, G. J.,;, Grosse-Kunstleve, R. W.,;, McCoy, A. J.,;, Moriarty, N. W.,;, Oeffner, R.,;, Read, R. J.,;, Richardson, D. C.,;, Richardson, J. S.,;, Terwilliger, T. C.,;, Zwart, P. H., Acta Crystallogr D Biol Crystallogr 2010, 66, 213-221.