Trimethylamine N-oxide (TMAO) and tert -butyl alcohol (TBA) at hydrophobic interfaces: Insights from molecular dynamics simulations

Langmuir

Volumn 29, Issue 25, 2013, Pages 8017-8024

  Fiore, Andrew ^a   Venkateshwaran, Vasudevan ^a   Garde, Shekhar ^a  

^a Rensselaer Polytechnic Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONCENTRATION DEPENDENCE; HYDROPHOBIC INTERFACE; INTERFACIAL STRUCTURES; MOLECULAR ARCHITECTURE; MOLECULAR DYNAMICS SIMULATIONS; OCTANE-WATER INTERFACE; SOLUTION CONCENTRATION; TRIMETHYLAMINE N OXIDES;

ALCOHOLS; BIOCHEMISTRY; FUNCTIONAL GROUPS; HYDROGEN BONDS; MOLECULAR DYNAMICS; SURFACE CHEMISTRY; VAPORS;

MOLECULES;

METHYLAMINE; TERT BUTYL ALCOHOL; TRIMETHYLOXAMINE;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; MOLECULAR DYNAMICS;

HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; METHYLAMINES; MOLECULAR DYNAMICS SIMULATION; TERT-BUTYL ALCOHOL;

EID: 84879521356     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la401203r     Document Type: Article

References (36)

1. Arakawa, T.; Timasheff, S. N. The stabilization of proteins by osmolytes Biophys. J. 1985, 47, 411
2. Yancey, P. H.; Clark, M. E.; Hand, S. C.; Bowlus, R. D.; Somero, G. N. Living with water-stress-evolution of osmolyte systems Science 1982, 217, 1214-1222
3. Wang, A.; Bolen, D. W. A naturally occurring protective system in urea-rich cells: mechanism of osmolyte protection of proteins against urea denaturation Biochemistry 1997, 36, 9101-9108
4. Street, T. O.; Bolen, D. W.; Rose, G. D. A molecular mechanism for osmolyte-induced protein stability Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 13997-14002
5. Zou, Q.; Bennion, B. J.; Daggett, V.; Murphy, K. P. The molecular mechanism of stabilization of proteins by TMAO and its ability to counteract the effects of urea J. Am. Chem. Soc. 2002, 124, 1192-1202
6. Athawale, M. V.; Dordick, J. S.; Garde, S. Osmolyte trimethylamine-N- oxide does not affect the strength of hydrophobic interactions: Origin of osmolyte compatibility Biophys. J. 2005, 89, 858-866
7. Canchi, D. R.; Jayasimha, P.; Rau, D. C.; Makhatadze, G. I.; Garcia, A. E. Molecular mechanism for the preferential exclusion of TMAO from protein surfaces J. Phys. Chem. B 2012, 116, 12095-12104
8. Anand, G.; Jamadagni, S. N.; Garde, S.; Belfort, G. Self-assembly of TMAO at hydrophobic interfaces and its effect on protein adsorption: Insights from experiments and simulations Langmuir 2010, 26, 9695-9702
9. Sagle, L. B.; Cimatu, K.; Litosh, V. A.; Liu, Y.; Flores, S. C.; Chen, X.; Yu, B.; Cremer, P. S. Methyl groups of trimethylamine N-oxide orient away from hydrophobic interfaces J. Am. Chem. Soc. 2011, 133, 18707-18712
10. Patel, H. A.; Nauman, E. B.; Garde, S. Molecular structure and hydrophobic solvation thermodynamics at an octane-water interface J. Chem. Phys. 2003, 119, 9199-9206
11. Patel, A. J.; Varilly, P.; Jamadagni, S. N.; Acharya, H.; Garde, S.; Chandler, D. Extended surfaces modulate hydrophobic interactions of neighboring solutes Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 17678-17683
12. Kita, Y.; Arakawa, T.; Lin, T.-Y.; Timasheff, S. N. Contribution of the surface free energy perturbation to protein-solvent interactions Biochemistry 1994, 33, 15178-15189
13. Berendsen, H.; Grigera, J.; Straatsma, T. The missing term in effective pair potentials J. Phys. Chem. 1987, 91, 6269-6271
14. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A 2nd generation force-field for the simulation of proteins, nucleic-acids, and organic-molecules J. Am. Chem. Soc. 1995, 117, 5179-5197
15. Kast, K. M.; Brickmann, J.; Kast, S. M.; Berry, R. S. Binary phases of aliphatic N-oxides and water: Force field development and molecular dynamics simulation J. Phys. Chem. A 2003, 107, 5342-5351
16. Hess, B.; Kutzner, C.; van der Spoel, D.; Lindahl, E. GROMACS 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation J. Chem. Theory Comput. 2008, 4, 435-447
17. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. Molecular dynamics with coupling to an external bath J. Chem. Phys. 1984, 81, 3684-3690
18. Bussi, G.; Donadio, D.; Parrinello, M. Canonical sampling through velocity rescaling J. Chem. Phys. 2007, 126, 014101
19. Darden, T.; York, D.; Pedersen, L. Particle Mesh Ewald-An N.LOG(N) method for ewald sums in large systems J. Chem. Phys. 1993, 98, 10089-10092
20. Allen, M.; Tildesley, D. Computer Simulation of Liquids; Clarendon Press: Oxford, 1999.
21. Hess, B.; Bekker, H.; Berendsen, H.; Fraaije, J. LINCS: A linear constraint solver for molecular simulations J. Comput. Chem. 1997, 18, 1463-1472
22. Schlossman, M. L.; Tikhonov, A. M. Molecular ordering and phase behavior of surfactants at water-oil interfaces as probed by X-ray surface scattering Annu. Rev. Phys. Chem. 2008, 59, 153-177
23. Paul, S.; Patey, G. N. Why tert-butyl alcohol associates in aqueous solution but trimethylamine-N-oxide does not J. Phys. Chem. B 2006, 110, 10514-10518
24. Gliński, J.; Chavepeyer, G.; Platten, J.-K. Surface properties of diluted aqueous solutions of tert-butyl alcohol J. Chem. Phys. 1995, 102, 2113
25. Patel, A. J.; Varilly, P.; Jamadagni, S. N.; Hagan, M. F.; Chandler, D.; Garde, S. Sitting at the edge: How biomolecules use hydrophobicity to tune their interactions and function J. Phys. Chem. B 2012, 116, 2498-2503
26. Willard, A. P.; Chandler, D. Instantaneous liquid interfaces J. Phys. Chem. B 2010, 114, 1954-1958
27. Gragson, D. E.; Richmond, G. L. Investigations of the structure and hydrogen bonding of water molecules at liquid surfaces by vibrational sum frequency spectroscopy J. Phys. Chem. B 1998, 102, 3847-3861
28. Lee, C.-Y.; McCammon, J. A.; Rossky, P. The structure of liquid water at an extended hydrophobic surface J. Chem. Phys. 1984, 80, 4448
29. Luzar, A.; Chandler, D. Hydrogen-bond kinetics in liquid water Nature 1996, 379, 55-57
30. Davis, J. G.; Gierszal, K. P.; Wang, P.; Ben-Amotz, D. Water structural transformation at molecular hydrophobic interfaces Nature 2012, 491, 582-585
31. Moore, F. G.; Richmond, G. L. Integration or segregation: How do molecules behave at oil/water interfaces? Acc. Chem. Res. 2008, 41, 739-748
32. Nelson, N.; Walder, R.; Schwartz, D. K. Single molecule dynamics on hydrophobic self-assembled monolayers Langmuir 2012, 28, 12108-12113
33. Auton, M.; Ferreon, A. C. M.; Bolen, D. W. Metrics that differentiate the origins of osmolyte effects on protein stability: A test of the surfacetension proposal J. Mol. Biol. 2006, 361, 983-992
34. Liao, Y. T.; Cremer, P. Private communication.
35. Subramanian, D.; Anisimov, M. A. Resolving the mystery of aqueous solutions of tertiary butyl alcohol J. Phys. Chem. B 2011, 115, 9179-9183
36. Subramanian, D.; Ivanov, D. A.; Yudin, I. K.; Anisimov, M. A.; Sengers, J. V. Mesoscale inhomogeneities in aqueous solutions of 3-methylpyridine and tertiary butyl alcohol J. Chem. Eng. Data 2011, 56, 1238-1248