Total syntheses of chiral sn-myo-inositol-1,4,5-trisphosphate1 and its enantiomer

✍ Scribed by Alexander E. Stepanov; Olga B. Runova; Gilbert Schlewer; Bernard Spiess; Vitaly I. Shvets

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 237 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93465-3

✦ Synopsis

sn-myo-Inositol-1,4,5_trisphophate (Ins(1,4,5)PJ) and its enantiomers are prepared by synthesis of suitably protected myo-inositols, separation of enantiomers via the formation of D-mannose diastereomeric derivatives and selective phosphorylations. sn~m~-Inositol-~,4,5-trisphosphate lns(1,4,5)?, (-)-a is a well known second messenger in living cells.2 To date, only chemical approaches could provide preparative quantities of inositol-phosphates for physico-chemical and biological investigations. Biological probes, labelled and modified inositol-phosphates can also be obtained only by synthetic means. During the last three years, several syntheses of chiral Ins(l,4,5)Ps have been reported. The separation of the enantiomers was achieved by the formation of diastereomeric esters using chiral acids such as l-menthoxyacetic acids or camphanic acid4 or by the use of glycosyl derivatives.5.6 Some separations of enantiomers were also performed by chiral HPLC methods.7 More recently a method using an enzymatic reaction has been proposed.* The aim of our program is to develop convenient methods for the total synthesis of Ins(1,4,5)Ps and derivatives 5'125