PuSH - Publication Server of Helmholtz Zentrum München: Enzyme-Assisted Total Synthesis of the Optical Antipodes <em>D-myo</em>-Inositol 3,4,5-Trisphosphate and <em>D-myo</em>-Inositol 1,5,6-Trisphosphate: Aspects of Their Structure-Activity Relationship to Biologically Active Inositol Phosphates.

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Adelt, S.* ; Plettenburg, O. ; Stricker, R.* ; Reiser, G.* ; Altenbach, H.J.* ; Vogel, G.*

Enzyme-Assisted Total Synthesis of the Optical Antipodes D-myo-Inositol 3,4,5-Trisphosphate and D-myo-Inositol 1,5,6-Trisphosphate: Aspects of Their Structure-Activity Relationship to Biologically Active Inositol Phosphates.

J. Med. Chem. 42, 1262-1273 (1999)

Open Access Green as soon as Postprint is submitted to ZB.

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Unambiguous total syntheses of both optical antipodes of the enantiomeric pair d-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P₃) and d-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P₃) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C₂-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P₄ and Ins(1,4,5,6)P₄ in three steps. With a recently identified and partially purified InsP₅/InsP₄ phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P₃ and Ins(1,5,6)P₃, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P₃/Ins(1,5,6)P₃ resemble those of Ins(1,2,3)P₃, a compound with antioxidant potential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42^IP4, a high-affinity Ins(1,3,4,5)P₄/PtdIns(3,4,5)P₃-specific binding protein from pig cerebellum.

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