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Synthesis of DL-myo-inositol 1-phosphate and its thiophosphate analogue

✍ Scribed by Thomas Metschies; Carsten Schultz; Bernd Jastorff

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 122 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)80381-0

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✦ Synopsis

A novel method for synthesis of myo-inositol l-phosphate using phosphorus oxychloride is described an transferred to synthesis of its thiophosphate analogue.

The inhibition of myo

-inositol l-phosphatase UP1 -ase) by lithium ions is used therapeutically in treating manic-depressive illnesses '*'s3. IP1 -ase is a key regulatory enzyme in phosphatidylinositol (PI) metabolism 4*5. Interestingly this enzyme is not enantioselective 4. Recently an anti-proliferative effect of lithium chloride on melanoma cells and its link to PI turnover was reported 6. Non-hydrolysable derivatives of myo-inositol l-phosphate 3 UP11 are potential inhibitors of the phosphatase and hence the phosphatidylinositol turnover. myo-Inositol I-thiophosphate S might be a candidate for antagonistic action In PI metabolism. Conventional methods for synthesis of IPt 7.8 have faIled for the thiophosphate. This prompted us to develop a novel method for synthesis of 3 which was transferred to thiophosphorylatlon later on.

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