Calculation of pKa values of carboxylic acids: Application to bilirubin

Journal of Molecular Structure: THEOCHEM

Volumn 947, Issue 1-3, 2010, Pages 76-82

  Borštnar, Rok ^a   Choudhury, Amrita Roy ^a   Stare, Jernej ^a   Novič, Marjana ^a   Mavri, Janez ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

Ab initio; Bilirubin; Bilitranslocase; Membrane transport; pKa

Indexed keywords

EID: 84961979187     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2010.01.043     Document Type: Article

References (60)

1. Passamonti S., Vanzo A., Vrhovšek U., Terdoslavich M., Cocolo A., Decorti G., and Mattivi F. Food Res. Int. 38 (2005) 953
2. Stocker R., Yamamoto Y., McDonagh A.F., Glazer A.N., and Ames B.N. Science 235 (1987) 1043
3. Underwood J.C.E. General and Systematic Pathology. fourth ed. (2004), Churchill Livingstone, Edinburgh
4. Ostrow J.D., Mukerjee P., and Tiribelli C. J. Lipid Res. 35 (1994) 1715
5. Zucker S.D., Goessling W., and Hoppin A.G. J. Biol. Chem. 274 (1991) 10852
6. Scharschmidt B.F., Waggoner J.G., and Berk P.D. J. Clin. Invest. 56 (1975) 1280
7. Berne R.M., and Levy M.N. Physiology. fourth ed. (1998), Mosby, Inc., New York
8. Paumgartner G., and Reichen J. Clin. Sci. Mol. Med. 51 (1976) 169
9. Manallack D.T. Persp. Med. Chem. 1 (2007) 25
10. Lightner D.A., Holmes D.L., and McDonagh A.F. J. Biol. Chem. 271 (1996) 2397
11. Boiadjiev S.E., Watters K., Wolf S., Lai B.N., Welch W.H., McDonagh A.F., and Lightner D.A. Biochemistry 43 (2004) 1561
12. Trull F.R., Boiadjiev S., Lightner D.A., and McDonagh A.F. J. Lipid Res. 38 (1997) 1178
13. Wade R.C., Raquet X., Lounnas V., and Lamotte-Brasseur J. Biophys. J. 73 (1997) 2416
14. Misra V.K., and Honig B. Proc. Natl. Acad. Sci. USA: Biophys. 92 (1995) 4691
15. Bashford D., and Karplus M. Biochemistry 29 (1990) 10219
16. McCammon J.A., and Nielsen J.E. Protein Sci. 12 (2003) 1894
17. Warshel A. Biochemistry 20 (1981) 3167
18. Pliego Jr. J.R., and Riveros J.M. J. Phys. Chem. A 106 (2002) 7434
19. Kelly C.P., Cramer C.J., and Truhlar D.G. J. Phys. Chem. A 110 (2006) 2493
20. Liptak M.D., and Shields G.C. J. Am. Chem. Soc. 123 (2001) 7314
21. Fu Y., Liu L., Li R.Q., Liu R., and Guo Q.X. J. Am. Chem. Soc. 126 (2004) 814
22. Ho J., and Coote M.L. J. Chem. Theory Comput. 5 (2009) 295
23. Magill A.M., Cavell K.J., and Yates B.F. J. Am. Chem. Soc. 126 (2004) 8717
24. Li G., and Cui Q. J. Phys. Chem. B 107 (2003) 14521
25. Riccardi D., and Cui Q. J. Phys. Chem. A 11 (2007) 5703
26. Riccardi D., Schaefer P., and Cui Q. J. Phys. Chem. B 109 (2005) 17715
27. Ghosh N., and Cui Q. J. Phys. Chem. B 112 (2008) 8387
28. Warshel A., Kamerlin S.C.L., and Haranczyk M. J. Phys. Chem. B 113 (2009) 1253
29. Miertus S., Scrocco E., and Tomasi J. Chem. Phys. 55 (1981) 117
30. Miertus S., and Tomasi J. Chem. Phys. 65 (1982) 239
31. Vianello R., and Maksić Z.B. Chem. Commun. 27 (2005) 3412
32. Vianello R., and Maksić Z.B. Eur. J. Org. Chem. 24 (2004) 5003
33. Vianello R., and Maksić Z.B. New J. Chem. 33 (2009) 739
34. Vianello R., and Maksić Z.B. Eur. J. Org. Chem. 16 (2005) 3571
35. Vianello R., and Maksić Z.B. New J. Chem. 32 (2008) 413
36. De Abreu H.A., De Almeida W.B., and Duarte H.A. Chem. Phys. Lett. 383 (2004) 47
37. Becke A.D. J. Chem. Phys. 98 (1993) 5648
38. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
39. Marcus Y. Ion Solvation (1985), Willey, New York
40. Lim C., Bashford D., and Karplus M. J. Phys. Chem. 95 (1991) 5610
41. Tissandier M.D., Cowen K.A., and Feng W.J. J. Phys. Chem. 102 (1998) 7787
42. Miertus S., Scrocco E., and Tomasi J. Chem. Phys. 55 (1981) 117
43. Tomasi J., Mennucci B., and Cammi R. Chem. Rev. 105 (2005) 2999
44. Florian J., and Warshel A. J. Phys. Chem. B 103 (1999) 10282
45. Florian J., and Warshel A. J. Phys. Chem. B 101 (1997) 5583
46. Strajbl M., Florian J., and Warshel A. J. Am. Chem. Soc. 122 (2000) 5354
47. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., 340 Quinnipiac Street, Building 40, Wallingford, CT, 06492, 2004, (Copyright C 1994-2003).
48. Mavri J., and Gaberšček M. Chem. Phys. Lett. 308 (1999) 421
49. Passamonti S., Battiston S., and Sottocasa G.L. Mol. Membr. Biol. 16 (1999) 167
50. Novič M., Passamonti S., Karawajczyk A., Drgan V., Medič N., and Oboh G. Biochem. Pharm. 73 (2007) 308
51. Passamonti S., Battiston S., and Sottocasa G.L. Eur. J. Biochem. 253 (1998) 84
52. Passamonti S., Battiston S., and Sottocasa G.L. FEBS Lett. 482 (2000) 167
53. Tiribelli C., Torres A.M., Lunazzi G.C., and Stremmel W. Proc. Natl. Acad. Sci. 90 (1993) 8136
54. Passamonti S., Cocolo A., Braidot E., Petrussa E., Peresson C., Medič N., Macri F., and Vianello A. FEBS J. 272 (2005) 3282
55. Passamonti S., Terdoslavich M., Margon A., Cocolo A., Medič N., Micali F., Decorti G., and Franko M. FEBS J. 272 (2005) 5522
56. John B. West (Ed.), Best and Taylor's: Physiological Basis of Medical Practice, twelfth ed., Williams & Wilkins, Baltimore, 1990, pp. 14-30.
57. Pitera J.W., and van Gunsteren W.F. J. Phys. Chem. B 105 (2001) 11264
58. Billeter S.R., and van Gunsteren W.F. J. Phys. Chem. A 104 (2000) 3276
59. Lee A.C., and Crippen G.M. J. Chem. Inf. Model. 49 (2009) 2013
60. Noyes R.M. J. Am. Chem. Soc. 84 (1962) 513