Synthesis of three enantiomeric pairs of scyllo-inositol phosphate and molecular interactions between all possible regioisomers of scyllo-inositol phosphate and inositol 1,4,5-trisphosphate 3-kinase

Bioorg Med Chem Lett. 2003 Sep 15;13(18):2981-4. doi: 10.1016/s0960-894x(03)00629-2.

Abstract

scyllo-Inositol phosphates, which are among the stereoisomers of myo-inositol phosphate, can have 15 possible regioisomers including three enantiomeric pairs: scyllo-I(1,2)P(2), scyllo-I(1,2,4)P(3), scyllo-I(1,2,3,4)P(4). We herein describe the facile synthetic routes to the three enantiomeric pairs of scyllo-inositol phosphate and the molecular interactions between 15 regioisomers of scyllo-inositol phosphate and inositol 1,4,5-trisphosphate 3-kinase. Geometry of the enzyme binding site is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Inhibitory Concentration 50
  • Inositol / chemical synthesis
  • Inositol / pharmacology
  • Inositol Phosphates / chemical synthesis*
  • Inositol Phosphates / pharmacology
  • Optical Rotation
  • Phosphotransferases (Alcohol Group Acceptor) / antagonists & inhibitors
  • Phosphotransferases (Alcohol Group Acceptor) / metabolism*
  • Protein Binding
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Inositol Phosphates
  • scyllitol
  • Inositol
  • Phosphotransferases (Alcohol Group Acceptor)
  • Inositol 1,4,5-trisphosphate 3-kinase