Hydrogen Bonding of 1,2-Azaborines in the Binding Cavity of T4 Lysozyme Mutants: Structures and Thermodynamics

Journal of the American Chemical Society

Volumn 138, Issue 37, 2016, Pages 12021-12024

  Lee, Hyelee ^a   Fischer, Marcus ^b   Shoichet, Brian K ^b   Liu, Shih Yuan ^a  

^a BOSTON COLLEGE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BINS; ENZYMES; THERMODYNAMICS;

BINDING CAVITY; BIOLOGICAL SETTINGS; HYDROGEN BOND DONORS; PROTEIN CRYSTALLOGRAPHY; T4 LYSOZYME;

HYDROGEN BONDS;

ALANINE; BENZENE DERIVATIVE; BORON DERIVATIVE; ETHYLBENZENE; GLUTAMINE; LEUCINE; LYSOZYME; METHIONINE; 1,2-AZABORINE;

ARTICLE; CALORIMETRY; ENTEROBACTERIA PHAGE T4; HYDROGEN BOND; ISOTHERMAL TITRATION CALORIMETRY; MUTANT; PROTEIN BINDING; PROTEIN CONFORMATION; QUANTITATIVE ANALYSIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; MOLECULAR MODEL;

BORON COMPOUNDS; CALORIMETRY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MURAMIDASE; THERMODYNAMICS;

EID: 84988674529     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b06566     Document Type: Article

References (47)

1. Liu, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2008, 47, 242 10.1002/anie.200703535
2. Bosdet, M. J. D.; Piers, W. E. Can. J. Chem. 2009, 87, 8 10.1139/v08-110
3. Campbell, P. G.; Marwitz, A. J. V.; Liu, S.-Y. Angew. Chem., Int. Ed. 2012, 51, 6074 10.1002/anie.201200063
4. Zhou, H.-B.; Nettles, K. W.; Bruning, J. B.; Kim, Y.; Joachimiak, A.; Sharma, S.; Carlson, K. E.; Stossi, F.; Katzenellenbogen, B. S.; Greene, G. L.; Katzenellenbogen, J. A. Chem. Biol. 2007, 14, 659 10.1016/j.chembiol.2007.04.009
5. Ito, H.; Yumura, K.; Saigo, K. Org. Lett. 2010, 12, 3386 10.1021/ol1012058
6. Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451 10.1021/jm200187y
7. McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348 10.1021/ed1003806
8. Liu, L.; Marwitz, A. J. V.; Matthews, B. W.; Liu, S.-Y. Angew. Chem., Int. Ed. 2009, 48, 6817 10.1002/anie.200903390
9. Knack, D. H.; Marshall, J. L.; Harlow, G. P.; Dudzik, A.; Szaleniec, M.; Liu, S.-Y.; Heider, J. Angew. Chem., Int. Ed. 2013, 52, 2599 10.1002/anie.201208351
10. Vlasceanu, A.; Jessing, M.; Kilburn, J. P. Bioorg. Med. Chem. 2015, 23, 4453 10.1016/j.bmc.2015.06.019
11. Rombouts, F. J.; Tovar, F.; Austin, N.; Tresadern, G.; Trabanco, A. A. J. Med. Chem. 2015, 58, 9287 10.1021/acs.jmedchem.5b01088
12. Marwitz, A. J. V.; Matus, M. H.; Zakharov, L. N.; Dixon, D. A.; Liu, S.-Y. Angew. Chem., Int. Ed. 2009, 48, 973 10.1002/anie.200805554
13. Chrostowska, A.; Xu, S.; Lamm, A. N.; Mazière, A.; Weber, C. D.; Dargelos, A.; Baylère, P.; Graciaa, A.; Liu, S.-Y. J. Am. Chem. Soc. 2012, 134, 10279 10.1021/ja303595z
14. Abbey, E. R.; Lamm, A. N.; Baggett, A. W.; Zakharov, L. N.; Liu, S.-Y. J. Am. Chem. Soc. 2013, 135, 12908 10.1021/ja4073436
15. Baggett, A. W.; Vasiliu, M.; Li, B.; Dixon, D. A.; Liu, S.-Y. J. Am. Chem. Soc. 2015, 137, 5536 10.1021/jacs.5b01916
16. Brown, A. N.; Li, B.; Liu, S.-Y. J. Am. Chem. Soc. 2015, 137, 8932 10.1021/jacs.5b05879
17. Amani, J.; Molander, G. A. Org. Lett. 2015, 17, 3624 10.1021/acs.orglett.5b01750
18. Wisniewski, S. R.; Guenther, C. L.; Argintaru, O. A.; Molander, G. A. J. Org. Chem. 2014, 79, 365 10.1021/jo402616w
19. Rudebusch, G. E.; Zakharov, L. N.; Liu, S.-Y. Angew. Chem., Int. Ed. 2013, 52, 9316 10.1002/anie.201304443
20. Barelier, S.; Sterling, T.; O'Meara, M. J.; Shoichet, B. K. ACS Chem. Biol. 2015, 10, 2772 10.1021/acschembio.5b00683
21. Liu, Z.; Wang, G.; Li, Z.; Wang, R. J. Chem. Theory Comput. 2008, 4, 1959 10.1021/ct800267x
22. Fersht, A. R.; Shi, J.-P.; Knill-Jones, J.; Lowe, D. M.; Wilkinson, A. J.; Blow, D. M.; Brick, P.; Carter, P.; Waye, M. M. Y.; Winter, G. Nature 1985, 314, 235 10.1038/314235a0
23. Gonzalez, A. Z.; Li, Z.; Beck, H. P.; Canon, J.; Chen, A.; Chow, D.; Duquette, J.; Eksterowicz, J.; Fox, B. M.; Fu, J.; Huang, X.; Houze, J.; Jin, L.; Li, Y.; Ling, Y.; Lo, M.-C.; Long, A. M.; McGee, L. R.; McIntosh, J.; Oliner, J. D.; Osgood, T.; Rew, Y.; Saiki, A. Y.; Shaffer, P.; Wortman, S.; Yakowec, P.; Yan, X.; Ye, Q.; Yu, D.; Zhao, X.; Zhou, J.; Olson, S. H.; Sun, D.; Medina, J. C. J. Med. Chem. 2014, 57, 2963 10.1021/jm401911v
24. Verner, E.; Katz, B. A.; Spencer, J. R.; Allen, D.; Hataye, J.; Hruzewicz, W.; Hui, H. C.; Kolesnikov, A.; Li, Y.; Luong, C.; Martelli, A.; Radika, K.; Rai, R.; She, M.; Shrader, W.; Sprengeler, P. A.; Trapp, S.; Wang, J.; Young, W. B.; Mackman, R. L. J. Med. Chem. 2001, 44, 2753 10.1021/jm0100638
25. Wang, Y.; Liu, Z.; Brunzelle, J. S.; Kovari, I. A.; Dewdney, T. G.; Reiter, S. J.; Kovari, L. C. Biochem. Biophys. Res. Commun. 2011, 412, 737 10.1016/j.bbrc.2011.08.045
26. Das, K.; Sarafianos, S. G.; Clark, A. D., Jr; Boyer, P. L.; Hughes, S. H.; Arnold, E. J. Mol. Biol. 2007, 365, 77 10.1016/j.jmb.2006.08.097
27. Foloppe, N.; Fisher, L. M.; Howes, R.; Kierstan, P.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. J. Med. Chem. 2005, 48, 4332 10.1021/jm049022c
28. Mills, J. E. J.; Dean, P. M. J. Comput.-Aided Mol. Des. 1996, 10, 607 10.1007/BF00134183
29. Toth, G.; Bowers, S. G.; Truong, A. P.; Probst, G. Curr. Pharm. Des. 2007, 13, 3476 10.2174/138161207782794284
30. Eriksson, A. E.; Baase, W. A.; Zhang, X.-J.; Heinz, D. W.; Blaber, M.; Baldwin, E. P.; Matthews, B. W. Science 1992, 255, 178 10.1126/science.1553543
31. Eriksson, A. E.; Baase, W. A.; Wozniak, J. A.; Matthews, B. W. Nature 1992, 355, 371 10.1038/355371a0
32. Morton, A.; Baase, W. A.; Matthews, B. W. Biochemistry 1995, 34, 8564 10.1021/bi00027a006
33. Wei, B. Q.; Baase, W. A.; Weaver, L. H.; Matthews, B. W.; Shoichet, B. K. J. Mol. Biol. 2002, 322, 339 10.1016/S0022-2836(02)00777-5
34. Morton, A.; Matthews, B. W. Biochemistry 1995, 34, 8576 10.1021/bi00027a007
35. Graves, A. P.; Shivakumar, D. M.; Boyce, S. E.; Jacobson, M. P.; Case, D. A.; Shoichet, B. K. J. Mol. Biol. 2008, 377, 914 10.1016/j.jmb.2008.01.049
36. Merski, M.; Fischer, M.; Balius, T. E.; Eidam, O.; Shoichet, B. K. Proc. Natl. Acad. Sci. U. S. A. 2015, 112, 5039 10.1073/pnas.1500806112
37. Eriksson, A. E.; Baase, W. A.; Matthews, B. W. J. Mol. Biol. 1993, 229, 747 10.1006/jmbi.1993.1077
38. Liu, L.; Baase, W. A.; Michael, M. M.; Matthews, B. W. Biochemistry 2009, 48, 8842 10.1021/bi900685j
39. Merski, M.; Shoichet, B. K. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 16179 10.1073/pnas.1208076109
40. Bissantz, C.; Kuhn, B.; Stahl, M. J. Med. Chem. 2010, 53, 5061 10.1021/jm100112j
41. Taylor, R.; Kennard, O.; Versichel, W. J. Am. Chem. Soc. 1983, 105, 5761 10.1021/ja00356a010
42. Tsai, C.-J.; Norel, R.; Wolfson, H. J.; Maizel, J. V.; Nussinov, R. Encyclopedia of Life Science; John Wiley & Sons, Ltd.: Chichester, 2001; doi: 10.1038/npg.els.0001343.
43. Perozzo, R.; Folkers, G.; Scapozza, L. J. Recept. Signal Transduction Res. 2004, 24, 1 10.1081/RRS-120037896
44. Cockroft, S. L.; Hunter, C. A. Chem. Soc. Rev. 2007, 36, 172 10.1039/B603842P
45. Camara-Campos, A.; Musumeci, D.; Hunter, C. A.; Turega, S. J. Am. Chem. Soc. 2009, 131, 18518 10.1021/ja9083495
46. Roth, T. A.; Minasov, G.; Morandi, S.; Prati, F.; Shoichet, B. K. Biochemistry 2003, 42, 14483 10.1021/bi035054a
47. Davis, A. A.; Teague, S. J. Angew. Chem., Int. Ed. 1999, 38, 736 10.1002/(SICI)1521-3773(19990315)38:6<736::AID-ANIE736>3.0.CO;2-Rfseq