Dissociation constants of water-insoluble carboxylic acids by13C-NMR. pKas of mesobiliverdin-XIIIα and mesobilirubin-XIIIα

Experientia

Volumn 52, Issue 6, 1996, Pages 639-642

  Lightner, D A ^a   Holmes, D L ^a   McDonagh, A F ^b  

^a UNIVERSITY OF NEVADA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Bilirubin; Biliverdin; Dicarboxylic acids; Dimethylsulfoxide

Indexed keywords

BILIRUBIN; BILIVERDIN; CARBOXYLIC ACID;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DISSOCIATION CONSTANT; PHYSICAL CHEMISTRY; SOLUBILITY;

BILIRUBIN; BILIVERDINE; CHEMISTRY, PHYSICAL; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SOLUBILITY; SOLUTIONS; WATER;

EID: 0029901219     PISSN: 00144754     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF01969747     Document Type: Article

References (30)

1. McDonagh, A. F., Bile pigments: Bilatrienes and 5.15-biladienes, in: The Porphyrins, vol. 6, p. 293. Ed. D. Dolphin Academic Press, New York 1979.
2. Carey, M., and Spivak, W., Physical chemistry of bile pigments and porphyrins with particular reference to bile, in: Bile Pigments and Jaundice, p. 81. Ed. J. D. Ostrow. Marcel Dekker, Inc., New York 1986.
3. Kolosov, I. V., and Shapolovenko, E. P., Zh. Obshc. Khim 47 (1977) 2149.
4. Hansen, P. E., Thiessen, H., and Brodersen, R., Acta Chem. Scand. B33 (1979) 281.
5. Moroi, Y., Matuura, R., and Hisadome. T., Bull. Chem. Soc Jpn. 58 (1985) 1426
6. Ostrow, J. D., Celic, L., and Mukerjee, P., J. Lipid Res. 29 (1988) 335.
7. Hahm, J.-S., Ostrow, J. D., Mukerjee, P., and Celic, L., J. Lipid Res. 13 (1992) 1123.
8. Serjeant, E. P., and Dempsey, B., Ionization Constants of Organic Acids in Aqueous Solution. Pergamon Press Ltd. Oxford 1979.
9. Ostrow, J. D., Mukerjee, P., and Tiribelli, C., J. Lipid Res. 35 (1994) 1715.
10. Overbeek, J. Th. G., Vink, C. L. J., and Deenstra, H., Recl. Trav. Chim. Pay-Bas 74 (1955) 81.
11. Brodersen, R., Aqueous solubility, albumin binding and tissue distribution of bilirubin, in: Bile Pigments and Jaundice. p. 158. Ed. J. D. Ostrow. Academic Press. New York 1986.
12. Hagen, R., and Roberts, J. D., J. Am chem. Soc. 91 (1968) 4504.
13. London, R. E., J. Magn. Reson. 38 (1980) 173.
14. Holmes, D. L., and Lightner, D. A., Tetrahedron 51 (1995) 1607.
15. King, E. J., Acid-base equilibria, vol. 4 under Topic 15 "Equilibrium properties of electrolyte solutions," (ed. R. A. Robinson) in the International Encyclopedia of Physical Chemistry and Chemical Physics Eds-in-chief E. A. Guggenheim, J. E. Mayer, and F. C. Tompkins. Pergamon Press Ltd Oxford 1965.
16. Lee, J. J., Daly, L. H., and Cowger, M. L., Res. Commun. Chem. Pathol. Pharmac. 9 (1974) 763.
17. Falk, H., The Chemistry of Linear Oligopyrroles and Bile Pigments. Springer-Verlag, Wien 1989.
18. Wagner, U. G., Müller, N., Schmitzberger, W., Falk, H., and Kratky, C., J. molec. Biol. 2117 (1995) 326.
19. Bonnett, R., Davies, J. E., Hursthouse, M. B., and Sheldrick, G. M., Proc. R. Soc. London, Ser. B 202 (1978) 249.
20. LeBas, G., Allegret, A., Mauguen, Y., DeRango, C., and Bailly, M., Acta Crystallogr., Sect. B B 36 (1980) 3007.
21. Person, R. V., Peterson, B. R., and Lightner, D. A., J. Am. chem. Soc. 116 (1994) 42.
22. Nogales, D., and Lightner, D. A., J. biol. Chem. 270 (1995) 73.
23. Mugnoli, A., Manitto, P., and Monti, D., Acta Crystallogr., Sect. C Cryst. Struct. Commun. 39 (1983) 1287.
24. Boiadjiev, S. E., Person, R. V., Puzicha, G., Knobler, C., Maverick, E., Trueblood, K. N., and Lightner, D. A., J. Am. chem. Soc. 114 (1992) 10123
25. Kaplan, D., and Navon, G., Israel J. Chem. 23 (1983) 177.
26. Eberson, L., Acidity and hydrogen bonding of carboxyl groups, in: The Chemistry of Carboxylic Acids and Esters chap. 6, p. 211. Ed. S. Patai. John Wiley & Sons. Ltd. London 1969.
27. Cistola, D. P., Small, D. M., and Hamilton, J. A., J. Lipid Res. 23 (1982) 795.
28. Cabral, D. P., Hamilton, J. A., and Small, D. M.. J. Lipid Res. 24 (1986) 334.
29. Nogales, D., and Lightner, D. A., J. labelled Cpds and Radiopharm. 34 (1994) 453.
30. Pu, Y. M., and Lightner, D. A., Tetrahedron 47 (1991) 6163.