Sequence-Specific, Nanomolar Peptide Binding via Cucurbit[8]uril-Induced Folding and Inclusion of Neighboring Side Chains

Journal of the American Chemical Society

Volumn 137, Issue 10, 2015, Pages 3663-3669

  Smith, Lauren C ^a   Leach, David G ^a   Blaylock, Brittney E ^a   Ali, Omar A ^a   Urbach, Adam R ^a  

^a TRINITY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; DISSOCIATION; ELECTROSPRAY IONIZATION; FLUORESCENCE; FLUORESCENT SCREENS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEINS; RECOMBINANT PROTEINS;

BIOLOGICAL APPLICATIONS; CHEMICAL EQUATIONS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; EQUILIBRIUM DISSOCIATION CONSTANT; FLUORESCENT INDICATORS; H NMR SPECTROSCOPY; ISOTHERMAL TITRATION CALORIMETRY; SYNTHETIC RECEPTORS;

PEPTIDES;

ALANINE; CUCURBITACIN; CUCURBIT[8]URIL; FLUORESCENT DYE; LEUCINE; RECOMBINANT PROTEIN; TETRAMETHYLBENZOBIS(IMIDAZOLIUM); TRIPEPTIDE; TYROSINE; UNCLASSIFIED DRUG; BRIDGED COMPOUND; CUCURBIT(8)URIL; IMIDAZOLE DERIVATIVE; OLIGOPEPTIDE; PEPTIDE LIBRARY; PHENYLALANINE; TYROSYL-LEUCYL-ALANINE;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING COMPETITION; DISSOCIATION CONSTANT; ELECTROSPRAY MASS SPECTROMETRY; FLUORESCENCE; ISOMER; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR RECOGNITION; PEPTIDE LIBRARY; PROTEIN BINDING; PROTEIN FOLDING; PROTEIN STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; PROTEIN MOTIF; THERMODYNAMICS;

AMINO ACID MOTIFS; AMINO ACID SEQUENCE; BRIDGED COMPOUNDS; IMIDAZOLES; OLIGOPEPTIDES; PEPTIDE LIBRARY; PHENYLALANINE; PROTEIN FOLDING; THERMODYNAMICS;

EID: 84925276278     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b00718     Document Type: Article

References (39)

1. Peng, H.-P.; Lee, K. H.; Jian, J.-W.; Yang, A.-S. Proc. Natl. Acad. Sci. U.S.A. 2014, 111, E2656
2. Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479
3. Yin, H.; Hamilton, A. D. Angew. Chem., Int. Ed. 2005, 44, 4130
4. Houk, K. N.; Leach, A. G.; Kim, S. P.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 4872
5. Schmuck, C. Synlett 2011, 1798
6. Urbach, A. R.; Ramalingam, V. Isr. J. Chem. 2011, 51, 664
7. Wright, A. T.; Griffin, M. J.; Zhong, Z. L.; McCleskey, S. C.; Anslyn, E. V.; McDevitt, J. T. Angew. Chem., Int. Ed. 2005, 44, 6375
8. Tashiro, S.; Tominaga, M.; Kawano, M.; Therrien, B.; Ozeki, T.; Fujita, M. J. Am. Chem. Soc. 2005, 127, 4546
9. Wehner, M.; Janssen, D.; Shafer, G.; Schrader, T. Eur. J. Org. Chem. 2006, 138
10. Lagona, L.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844
11. Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959
12. Rekharsky, M. V.; Mori, T.; Yang, C.; Young, H. K.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A. E.; Liu, S.; Isaacs, L.; Chen, W.; Moghaddam, S.; Gilson, M. K.; Kim, O.; Inoue, Y. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 20737
13. Cao, L.; Sekotur, M.; Zavalij, P. Y.; Mlinaric-Majerski, M.; Glaser, R.; Isaacs, L. Angew. Chem., Int. Ed. 2014, 53, 988
14. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H. J.; Kim, K. Acc. Chem. Res. 2003, 36, 621
15. Liu, S. M.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 16798
16. Lagona, L.; Fettinger, J.; Isaacs, L. J. Org. Chem. 2005, 70, 10381
17. Isaacs, L.; Park, S.-K.; Liu, S. M.; Ko, Y. H.; Selvapalam, N.; Kim, Y.; Kim, H.; Zavalij, P. Y.; Kim, G.-H.; Lee, H.-S.; Kim, K. J. Am. Chem. Soc. 2005, 127, 18000
18. Huang, W. H.; Liu, S. M.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2006, 128, 14744
19. Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267
20. Vinciguerra, B.; Cao, L.; Cannon, J. R.; Zavalij, P. Y.; Fenselau, C.; Isaacs, L. J. Am. Chem. Soc. 2012, 134, 13133
21. Lucas, D.; Isaacs, L. Org. Lett. 2011, 13, 4112
22. Nau, W. M.; Scherman, O. A. Isr. J. Chem. 2011, 51, 492
23. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540
24. Kim, H.-J.; Heo, J.; Jeon, W. S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 1526
25. Bush, M. E.; Bouley, N. D.; Urbach, A. R. J. Am. Chem. Soc. 2005, 127, 14511
26. Ali, O. A.; Olson, E. M.; Urbach, A. R. Supramol. Chem. 2013, 25, 863
27. Biedermann, F.; Rauwald, U.; Cziferszky, M.; Williams, K. A.; Gann, L. D.; Guo, B. Y.; Urbach, A. R.; Bielawski, C. W.; Scherman, O. A. Chem.-Eur. J. 2010, 16, 13716
28. Heitmann, L. M.; Taylor, A. B.; Hart, P. J.; Urbach, A. R. J. Am. Chem. Soc. 2006, 128, 12574
29. Moon, K.; Kaifer, A. E. Org. Lett. 2004, 6, 185
30. Tashiro, S.; Kobayashi, M.; Fujita, M. J. Am. Chem. Soc. 2006, 128, 9280
31. Dolain, C.; Hatakeyama, Y.; Sawada, T.; Tashiro, S.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 5564
32. Hatakeyama, Y.; Sawada, T.; Kawano, M.; Fujita, M. Angew. Chem., Int. Ed. 2009, 48, 8695
33. This value was obtained by titration in the presence of 100-fold excess MBBI as a weak competitor (Figure S45).
34. Rekharsky, M. V.; Yamamura, H.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y. Chem. Commun. 2008, 2236
35. Chinai, J. M.; Taylor, A. B.; Ryno, L. M.; Hargreaves, N. D.; Morris, C. A.; Hart, P. J.; Urbach, A. R. J. Am. Chem. Soc. 2011, 133, 8810
36. Ramalingam, V.; Kwee, S. K.; Ryno, L. M.; Urbach, A. R. Org. Biomol. Chem. 2012, 10, 8587
37. Nguyen, H. D.; Dang, D. T.; van Dongen, J. L. J.; Brunsveld, L. Angew. Chem., Int. Ed. 2010, 49, 895
38. Dang, D. T.; Nguyen, H. D.; Merkx, M.; Brunsveld, L. Angew. Chem., Int. Ed. 2013, 52, 2915
39. Gonzalez-Campo, A.; Brasch, M.; Uhlenheuer, D. A.; Gomez-Casado, A.; Yang, L.; Brunsveld, L.; Huskens, J.; Jonkheijm, P. Langmuir 2012, 28, 16364