Synthesis of Inositol 1,2-(cyclic)-4,5-trisphosphate

• Published in: Proceedings of the National Academy of Sciences - PNAS Vol. 84; no. 5; pp. 1206 - 1209
• Main Authors: Auchus, Richard J., Kaiser, Susan L., Majerus, Philip W.
• Format: Journal Article
• Language: English
• Published: Washington, DC National Academy of Sciences of the United States of America 01.03.1987; National Acad Sciences
• Subjects: Biochemistry; Biological and medical sciences; Cell metabolism, cell oxidation; Cell physiology; Chromatography, High Pressure Liquid; Elution; Formates; Fundamental and applied biological sciences. Psychology; Indicators and Reagents; Inositol phosphates; Inositol Phosphates - chemical synthesis; Inositols; Magnetic Resonance Spectroscopy; Molecular and cellular biology; Phosphates; Phospholipids; Phosphorus Radioisotopes; Quaternary ammonium compounds; Room temperature; Spectroscopy; Sugar Phosphates - chemical synthesis; Regulation(control); Method; Metabolism; Chemical synthesis; Cell; Inositophospholipide
• ISSN: 0027-8424; 1091-6490
• DOI: 10.1073/pnas.84.5.1206

We have developed a method for synthesis of inositol 1,2-(cyclic)-4,5-trisphosphate from inositol 1,4,5-trisphosphate using a water-solable carbodiimide. We obtained 1-1.5 μ mol of the inositol cyclic trisphosphate starting with 5 μ mol of inositol 1,4,5-trisphosphate. The cyclized product was isolated by HPLC on Partisil SAX. The identity of the cyclic product was verified by its hydrolysis to inositol 1,4,5-trisphosphate in acid and by its conversion to 1,2-(cyclic)-4-bisphosphate by a specific 5-phosphomonoesterase from platelets. We also identified the product by31P NMR spectroscopy, which showed a peak at 17.2 ppm, characteristic of a fivemembered cyclic phosphodiester ring, and peaks at 4.1 ppm and 0.8 ppm, indicative of phosphomonoesters. This relatively simple method for producing inositol 1,2-(cyclic)-4,5-trisphosphate will facilitate studies of the physiology of this compound in signal transduction.