Literature DB >> 8698102

Dissociation constants of water-insoluble carboxylic acids by 13C-NMR. pK(a)s of mesobiliverdin-XIII alpha and mesobilirubin-XIII alpha.

D A Lightner1, D L Holmes, A F McDonagh.   

Abstract

High-field 13C-NMR of 13C-enriched compounds in dilute aqueous d6-Me2-SO solutions provides a simple, accurate method for measuring pK(a)s of sparingly soluble carboxylic acids. Using this method, we found the pK(a)s of mesobilirubin-XIII alpha to be 4.2 and 4.9, much lower values than reported recently for bilirubin, and of mesobiliverdin-XIII alpha to be 3.9 and 5.3.

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Year:  1996        PMID： 8698102     DOI： 10.1007/bf01969747

Source DB:  PubMed          Journal:  Experientia        ISSN： 0014-4754


  10 in total

1.  The structure of bilirubin.

Authors:  R Bonnett; J E Davies; M B Hursthouse; G M Sheldrick
Journal:  Proc R Soc Lond B Biol Sci       Date:  1978-06-23

2.  Bilirubin ionic equilibria: their effects on spectra and on conformation.

Authors:  J J Lee; L H Daly; M L Cowger
Journal:  Res Commun Chem Pathol Pharmacol       Date:  1974-12

Review 3.  Structure and binding of unconjugated bilirubin: relevance for physiological and pathophysiological function.

Authors:  J D Ostrow; P Mukerjee; C Tiribelli
Journal:  J Lipid Res       Date:  1994-10       Impact factor: 5.922

4.  Structure determination of the biliverdin apomyoglobin complex: crystal structure analysis of two crystal forms at 1.4 and 1.5 A resolution.

Authors:  U G Wagner; N Müller; W Schmitzberger; H Falk; C Kratky
Journal:  J Mol Biol       Date:  1995-03-24       Impact factor: 5.469

5.  Bilirubin acidity. Titrimetric and 13C NMR studies.

Authors:  P E Hansen; H Thiessen; R Brodersen
Journal:  Acta Chem Scand B       Date:  1979

6.  Molecular and micellar associations in the pH-dependent stable and metastable dissolution of unconjugated bilirubin by bile salts.

Authors:  J D Ostrow; L Celic; P Mukerjee
Journal:  J Lipid Res       Date:  1988-03       Impact factor: 5.922

7.  Ionization behavior of aqueous short-chain carboxylic acids: a carbon-13 NMR study.

Authors:  D P Cistola; D M Small; J A Hamilton
Journal:  J Lipid Res       Date:  1982-07       Impact factor: 5.922

8.  The ionization behavior of bile acids in different aqueous environments.

Authors:  D J Cabral; J A Hamilton; D M Small
Journal:  J Lipid Res       Date:  1986-03       Impact factor: 5.922

9.  Ionization and self-association of unconjugated bilirubin, determined by rapid solvent partition from chloroform, with further studies of bilirubin solubility.

Authors:  J S Hahm; J D Ostrow; P Mukerjee; L Celic
Journal:  J Lipid Res       Date:  1992-08       Impact factor: 5.922

10.  On the structure of bilirubin in solution. 13C[1H] heteronuclear Overhauser effect NMR analyses in aqueous buffer and organic solvents.

Authors:  D Nogales; D A Lightner
Journal:  J Biol Chem       Date:  1995-01-06       Impact factor: 5.157
  10 in total
  3 in total

1.  Interactions of unconjugated bilirubin with vesicles, cyclodextrins and micelles: new modeling and the role of high pKa values.

Authors:  Pasupati Mukerjee; J Donald Ostrow
Journal:  BMC Biochem       Date:  2010-03-29       Impact factor: 4.059

Review 2.  Review: Bilirubin pKa studies: new models and theories indicate high pKa values in water, dimethylformamide and DMSO.

Authors:  Pasupati Mukerjee; J Donald Ostrow
Journal:  BMC Biochem       Date:  2010-03-29       Impact factor: 4.059

3.  Low solubility of unconjugated bilirubin in dimethylsulfoxide--water systems: implications for pKa determinations.

Authors:  Pasupati Mukerjee; J Donald Ostrow; Claudio Tiribelli
Journal:  BMC Biochem       Date:  2002-06-17       Impact factor: 4.059
  3 in total

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