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Synthesis of tritium‐labelled enantiomers of myo ‐inositol 1,4,5‐trisphosphate
Author(s) -
Marecek James F.,
Prestwich Glenn D.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270808
Subject(s) - chemistry , enantiomer , diastereomer , yield (engineering) , inositol , ketone , cyclitol , derivative (finance) , stereochemistry , tritium , total synthesis , organic chemistry , biochemistry , receptor , physics , economics , financial economics , nuclear physics , metallurgy , materials science
Both natural D‐ and L‐enantiomers of myo ‐Ins(1,4,5)P 3 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 chiral ketone with sodium borotritide and manipulation of protecting groups gave the enantiomeric [1‐ 3 H]‐2,3,6‐tri‐0‐benzyl‐ myo ‐inositols in 55% radiochemical yield. Phosphorylation with tetrabenzylpyrophosphate and complete hydrogenolytic debenzylation provided the separate D‐ myo and L‐ myo ‐ [1‐ 3 H]‐Ins(1,4,5)P 3 enantiomers in 30% radiochemical yield.