Synthesis of phosphatase-resistant analogues of phytic acid (InsP6)

Phytic acid is enzymatically catabolized to numerous inositol polyphosphates and subsequently to myo-inositol and inorganic phosphate. These conversions are important in energy metabolism, metabolic regulation, and signal transduction pathways. A concise synthesis of phosphatase-resistant analogues of phytic acid (InsP6) is described in which the P-1 phosphate has been replaced by phosphorothioate, phosphoroselenate, or methylphosphonate moieties. In addition, a new synthesis of P-1 tethered aminoalkyl InsP6 and the corresponding affinity resin are described.