Phospholipids chiral at phosphorus: Synthesis of dioleoylthiophosphatidylcholine and stereospecificity of lecithin-cholesterol acyltransferase

Theresa Rosario-Jansen, Henry Pownal, Ru Tai Jiang, Ming Daw Tsai

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Chiral 1,2-dioleoyl-sn-glycero-3-thiophosphocholine (DOPsC) was synthesized from chiral 1,2-dipalmitoyl-sn-glycero-3-thiophosphocholine (DPPsC) via hydrolysis to sn-glycero-3-thiophosphatidylcholine followed by reacylation. Both DOPsC and DPPsC were used to probe the stereochemical requirement in the enzyme-substrate recognition of lecithincholesterol acyltransferase (LCAT) from human plasma. In contrast to phospholipase A2, LCAT is totally insensitive to sulfur substitution or configuration at phosphorus and gives indistinguishable Km and Vmax values to Rp and Sp isomers of DOPsC and DPPsC and the corresponding natural substrates. The results suggest lack of stereospecific interaction between LCAT and the phosphate group of phospholipids.

Original languageEnglish (US)
Pages (from-to)179-184
Number of pages6
JournalBioorganic Chemistry
Volume18
Issue number2
DOIs
StatePublished - Jun 1990

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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