Synthesis and iron binding studies of myo-inositol 1,2,3-trisphosphate and (+/-)-myo-inositol 1,2-bisphosphate, and iron binding studies of all myo-inositol tetrakisphosphates

Ian D. Spiers, Christopher J. Barker, Sung-Kee Chung, Young-Tae Chang, Sally Freeman, John M. Gardiner, Peter H. Hirst, Peter A. Lambert, Robert H. Michell, David R. Poyner, Carl H. Schwalbe, Anthony W. Smith, Kevin R. H. Solomons

Research output: Contribution to journalArticlepeer-review

Abstract

The first syntheses of the natural products myo-inositol 1,2,3-trisphosphate and (+/-)-myo-inositol 1,2-bisphosphate are described. The protected key intermediates 4,5,6-tri-O-benzoyl-myo-inositol and (+/-)-3,4,5,6-tetra-O-benzyl-myo-inositol were phosphorylated with dibenzyl N,N-di-isopropylphosphoramidite in the presence of 1H-tetrazole and subsequent oxidation of the phosphite. The crystal structures of the synthetic intermediates (+/-)-1-O-(tert-butyldiphenylsilyl)-2,3,O-cyclohexylidene-myo-inos itol and (+/-)-4,5,6-tri-O-benzoyl-1-O-(tert-butyldiphenylsilyl)-2,3-O-cycl ohexylidene- myo-inositol are reported. myo-Inositol 1,2,3-trisphosphate (+/-)-myo-inositol 1,2-bisphosphate, and all isomeric myo-inositol tetrakisphosphates were evaluated for their ability to alter HO. production in the iron-catalysed Haber-Weiss reaction. The results demonstrated that a 1,2,3-grouping of phosphates in myo-inositol was necessary for inhibition also that (+/-)-myo-inositol 1,2-bisphosphate potentiated HO. production. myo-Inositol 1,2,3-trisphosphate resembled myo-inositol hexakisphosphate (phytic acid) in its ability to act as a siderophore by promoting iron-uptake into Pseudomonas aeruginosa.
Original languageEnglish
Pages (from-to)81-99
Number of pages19
JournalCarbohydrate Research
Volume282
Issue number1
DOIs
Publication statusPublished - 11 Oct 1996

Keywords

  • Binding
  • sites
  • biological transport crystallography
  • x-ray
  • hydroxyl
  • radical indicators
  • reagents
  • inositol
  • phosphates
  • iron models
  • molecular conformation
  • molecular structure
  • phytic acid
  • pseudomonas
  • aeruginosa
  • structure-activity relationship

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