Cholesterol ester hydrolase mediated conjugation of haloethanols with fatty acids

Hari K. Bhat, Ghulam Ansari

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The formation of fatty acid conjugates of haloethanols was studied under in vitro conditions by using purified bovine pancreatic cholesterol ester hydrolase (EC 3.1.1.13). The enzymatic formation of 2-chloroethyl and 2-bromoethyl esters of oleic, linoleic, linolenic, and arachidonic acids was confirmed by proton nuclear magnetic resonance spectroscopy and chemical ionization mass spectrometry. 2-Bromoethanol was a better substrate than 2-chloroethanol for fatty acid esterification using cholesterol ester hydrolase. Among the chloroethanols, 2-chloroethanol was a better substrate than 2,2-dichloroethanol and 2,2,2-trichloroethanol. The saturated fatty acids (palmitic and stearic) showed a small amount of ester formation when cholesterol ester hydrolase was used. The kinetics of haloethanol and oleic acid incorporation into haloethyl oleate catalyzed by cholesterol ester hydrolase were determined. In vitro experiments were also conducted to study the conjugation of haloethanols with fatty acids using rat liver microsomes. The saturated fatty acid (palmitic) was more reactive compared to unsaturated fatty acid (oleic) when haloethanols were used. The results using rat liver microsomes were in contrast to those obtained when cholesterol ester hydrolase was used. The synthesis, purification, and characterization of 2-chloroethyl and 2-bromoethyl esters of oleic, linoleic, linolenic, and arachidonic acids are also described.

Original languageEnglish (US)
Pages (from-to)311-317
Number of pages7
JournalChemical Research in Toxicology
Volume3
Issue number4
StatePublished - 1990

Fingerprint

Sterol Esterase
Fatty Acids
Linolenic Acids
Oleic Acids
Linoleic Acids
Arachidonic Acids
Esters
Liver Microsomes
Oleic Acid
Liver
Rats
Esterification
Substrates
Unsaturated Fatty Acids
Nuclear magnetic resonance spectroscopy
Ionization
Purification
Mass spectrometry
Mass Spectrometry
Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Toxicology
  • Health, Toxicology and Mutagenesis

Cite this

Cholesterol ester hydrolase mediated conjugation of haloethanols with fatty acids. / Bhat, Hari K.; Ansari, Ghulam.

In: Chemical Research in Toxicology, Vol. 3, No. 4, 1990, p. 311-317.

Research output: Contribution to journalArticle

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