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Synthesis of tritium-labelled enantiomers of myo-inositol 1,4,5-trisphosphate

โœ Scribed by James F. Marecek; Glenn D. Prestwich

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
371 KB
Volume
27
Category
Article
ISSN
0022-2135

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โœฆ Synopsis

Both natural D-and L-enantiomers of myo-lns(l,4,5)P3 were synthesized with specific activities 14-16 Ci/mmol. A suitable inositol derivative was resolved as the diastereomeric camphanate esters, and the chiral inositol derivatives were oxidized to the protected inosose. Reduction of each chirai ketone with sodium borotritide and mani ulation of protecting groups gave the enantiomeric [l -&-l]-2,3,6-tri-O-benzyl-myo-inositols in 55% radiochemical yield. Phosphorylation with tetrabenzylpyrophosphate and complete hydrogenolytic debenzylation provided the separate D-myo and L-my@ [1-3H]-lns(l,4,5)P3 enantiomers in 30% radiochemical yield.

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