Inhibitors of lipid phosphatidate receptors

N-palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids

Robert Bittman, Bernadette Swords, Károly Liliom, Gabor Tigyi

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

An improved synthesis of two lipid phosphoric acids, N-palmitoyl-L-serine phosphoric acid (NP-Ser-PA) and N-palmitoyl-L-tyrosine phosphoric acid (NP-Tyr-PA), from the benzyl esters of L-serine and L-tyrosine is described. The sequence of N-acylation, followed by phosphitylation with N,N-diisopropyi dibenzyl phosphoramidite, oxidation to the corresponding phosphate triesters, and simultaneous debenzylation of the dibenzyl phosphate and benzyl carboxylic esters gave NP-Ser-PA and NP-Tyr-PA in high overall yields. NP-Ser-PA and NP-Tyr-PA and their D stereoisomers were potent reversible inhibitors of the lysophosphatidic acid receptors expressed in Xenopus oocytes, thus providing prototypic structures for the development of inhibitors of the lysophosphatidate family of phospholipid growth factors.

Original languageEnglish (US)
Pages (from-to)391-398
Number of pages8
JournalJournal of Lipid Research
Volume37
Issue number2
StatePublished - Feb 1 1996

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Serine
Tyrosine
Lipids
Phosphoric Acids
Lysophosphatidic Acid Receptors
Phosphates
Stereoisomerism
Acylation
Organophosphates
Esters
Xenopus
Oocytes
Phospholipids
Intercellular Signaling Peptides and Proteins
N-palmitoyltyrosine phosphoric acid
phosphoric acid
N-palmitoylserine phosphoric acid
Oxidation

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Endocrinology
  • Cell Biology

Cite this

Inhibitors of lipid phosphatidate receptors : N-palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids. / Bittman, Robert; Swords, Bernadette; Liliom, Károly; Tigyi, Gabor.

In: Journal of Lipid Research, Vol. 37, No. 2, 01.02.1996, p. 391-398.

Research output: Contribution to journalArticle

Bittman, Robert ; Swords, Bernadette ; Liliom, Károly ; Tigyi, Gabor. / Inhibitors of lipid phosphatidate receptors : N-palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids. In: Journal of Lipid Research. 1996 ; Vol. 37, No. 2. pp. 391-398.
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