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. 1969 Jun;113(2):291–298. doi: 10.1042/bj1130291

Isolation of choline esters from aqueous solutions by extraction with sodium tetraphenylboron in organic solvents

F Fonnum 1
PMCID: PMC1184635  PMID: 5808318

Abstract

1. The method is based on the observation that choline esters and sodium tetraphenylboron (Kalignost) form complexes that are insoluble in water but soluble in organic solvents such as nitriles, higher ketones and benzyl alcohol. 2. The extraction procedure is an example of liquid cation exchange where tetraphenylboron is the cation-exchange group. 3. The proportion of choline esters extracted depends on the type and total amount of cation in the aqueous phase and the amount of sodium tetraphenylboron in the organic solvent. 4. The proportion of choline esters extracted is independent of the choline ester concentration, the pH (between 8 and 3) and the relative volumes of the two phases. 5. The affinity of sodium tetraphenylboron for choline esters increases with an increase in the size of the acyl group. 6. The choline ester extracted can be released into an aqueous solution by treatment with strong acids, silver salts and anion-exchange resins.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Ewins A. J. Acetylcholine, a New Active Principle of Ergot. Biochem J. 1914 Feb;8(1):44–49. doi: 10.1042/bj0080044. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Fonnum F. A radiochemical method for the estimation of choline acetyltransferase. Biochem J. 1966 Aug;100(2):479–484. doi: 10.1042/bj1000479. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Fonnum F. Choline acetyltransferase binding to and release from membranes. Biochem J. 1968 Sep;109(3):389–398. doi: 10.1042/bj1090389. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Fonnum F. Extraction of acetylcholine from aqueous solutions. Biochem Pharmacol. 1968 Dec;17(12):2503–2505. doi: 10.1016/0006-2952(68)90146-9. [DOI] [PubMed] [Google Scholar]
  5. GARDINER J. E., WITTAKER V. P. The identification of propionycholine as a constituent of ox spleen. Biochem J. 1954 Sep;58(1):24–29. doi: 10.1042/bj0580024. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Johnston G. A., Lloyd H. J., Stone N. Liquid cation exchange extraction of cholinomimetic activity from brain. J Neurochem. 1968 May;15(5):361–365. doi: 10.1111/j.1471-4159.1968.tb11622.x. [DOI] [PubMed] [Google Scholar]
  7. KHYM J. X. THE USE OF AMINES IN LIQUID-LIQUID EXTRACTIONS OF NUCLEIC ACIDS AND RELATED COMPOUNDS. Biochemistry. 1963 May-Jun;2:401–406. doi: 10.1021/bi00903a001. [DOI] [PubMed] [Google Scholar]
  8. MARQUARDT P., VOGG G. Uber einen empfindlichen Nachweis des Cholins und Acetylcholins mit Hilfe von Tetraphenyl-bor-natrium. Hoppe Seylers Z Physiol Chem. 1952;291(3):143–147. [PubMed] [Google Scholar]
  9. Marchbanks R. M. Exchangeability of radioactive acetylcholine with the bound acetylcholine of synaptosomes and synaptic vesicles. Biochem J. 1968 Jan;106(1):87–95. doi: 10.1042/bj1060087. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Potter L. T., Murphy W. Electrophoresis of acetylcholine, choline and related compounds. Biochem Pharmacol. 1967 Jul 7;16(7):1386–1388. doi: 10.1016/0006-2952(67)90174-8. [DOI] [PubMed] [Google Scholar]
  11. Temple D. M., Gillespie R. Liquid ion-exchange extraction of some physiologically active amines. Nature. 1966 Feb 12;209(5024):714–715. doi: 10.1038/209714a0. [DOI] [PubMed] [Google Scholar]
  12. Winteringham F. P., Disney R. W. A radiometric study of cholinesterase and its inhibition. Biochem J. 1964 Jun;91(3):506–514. doi: 10.1042/bj0910506. [DOI] [PMC free article] [PubMed] [Google Scholar]

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