De novo synthesis of the enantiomers Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 -regiospecificity of their enzymatic dephosphorylation

(T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is prese nted. Starting from p-benzoquinone, we took advantage of the C-2-symmetry o f conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable an d to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.