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Synthesis of mixtures of [ 2 H 6 ] myo ‐inositol monophosphates suitable as internal standards for quantitative GC/MS and a simple synthesis of DL‐ myo ‐inositol‐1‐phosphate
Author(s) -
Ghosh Suchitra,
Sherman William R.
Publication year - 1990
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.2580280208
Subject(s) - chemistry , inositol , phosphate , inositol phosphate , cyclitol , sugar phosphates , stereochemistry , chromatography , organic chemistry , biochemistry , receptor
Abstract A mixture of DL‐[ 2 H 6 ] myo ‐inositol‐1‐ and ‐4‐phosphate and (meso) myo ‐inositol‐2‐ and ‐5‐phosphate is readily prepared on a 100 milligram scale from the mixed isomers of di‐ O ‐cyclohexylidene‐[ 2 H 6 ] myo ‐inositol by phosphorylation with tetrabenzylpyrophosphate. The deblocked [ 2 H 6 ] myo ‐inositol monophosphate isomers are obtained where the relative amounts of racemic myo ‐inositol‐1‐phosphate ≥ ‐4‐phosphate ≥ ‐2‐phosphate ≥ ‐5‐phosphate. In addition a simple synthesis of DL‐myo‐inositol‐1‐phosphate was developed which was found to be unsatisfactory for the preparation of deuterium‐labeled product.