Preparation of ω-functionalized eicosane-phosphate building blocks

Istvan Jablonkai, Peter Oroszlan

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

New 1,20-substituted eicosanes carrying phosphate headgroups and readily derivatizable thiol, maleimido, and activated carboxylic ester moieties were prepared. The C 20-backbone of these molecules was assembled by a halopolycarbon homologation from 1,8-dichlorooctane and 1,6-dibromohexane. 20-Mercapto- and 20-maleimido-icosylphosphates were synthesized via ω-bromo di-t-butyl protected icosylphosphate while 20-phosphonooxy- icosanoic acid N-hydroxysuccinimidoyl ester was prepared via ω-bromo dibenzyl protected icosylphosphate in multistep syntheses. These molecules can serve as model compounds for studying binding and structural organization on different surfaces with potential applications in the fields of biosensors.

Original languageEnglish
Pages (from-to)103-112
Number of pages10
JournalChemistry and Physics of Lipids
Volume133
Issue number1
DOIs
Publication statusPublished - Jan 1 2005

Keywords

  • Bifunctional
  • Eicosane
  • Lipid
  • Phosphate
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

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