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Phosphatidyl inositol isopropylidene derivatives: synthesis, characterizaton and use as synthetic intermediates

✍ Scribed by Naoki Noda; Roy W. Keenan


Book ID
103040926
Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
783 KB
Volume
53
Category
Article
ISSN
0009-3084

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✦ Synopsis


To provide starting material for the synthesis of phosphatidyl inositol phosphates and inositol phosphates, isopropylidenes of phosphatidyl inositols were prepared. Phosphatidyl inositol obtained from yeast was converted into a mono-and two di-O-isopropylidenes fractions by transacetalation with 2,2-dimethoxypropane. Three isopropylidenes fractions were isolated and characterized by mass spectral analysis and comparison of the hydrolysis products of these fractions to know isopropylidenes of myo-inositol. The isopropylidenes were phosphatidtyl-2,3-O-isopropylidene-inositois, phosphatidyl-2,3:4,5-di-O-isopropylideneinositols and phosphatidyl-2,3:5,6-di-O-isopropylidene-inositols. These compounds are intermediates for the stereospecifie synthesis of different phosphatidyl inositol phosphates, inositol phosphates and analogs of these compounds. Using the di-O-isopropylidenes as starting materials, both phosphatidyl inositol-4-phosphate and phosphatidyl inositoi-6-phosphates were synthesized. Neither compound had been prepared synthetically before and phosphatidyl inositol-6-phosphate is not naturally occurring.


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