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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

The first syntheses of the natural products myo-inositol 1,2,3-trisphosphate and (±)-myoinositol 1,2-bisphosphate are described. The protected key intermediates 4,5,6-tri-O-benzoyl-myoinositol and (±)-3,4,5,6-tetra-O-benzyl-myo-inositol were phosphorylated with dibenzyl N,N-diisopropylphosphoramidite 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-inositol and (±)-4,5,6-tri-O-benzoyl-1-O-(tert-butyldiphenylsilyl)-2,3-O-cyclohexy lidene-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 - 28 Feb 1996
Externally publishedYes

Keywords

  • (±)-myo-Inositol 1,2-bisphosphate
  • antioxidant
  • myo-Inositol 1,2,3-trisphosphate
  • myo-Inositol tetrakisphosphates
  • siderophore

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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