title: Formation of methylphosphoryl inositol phosphates by extractions that employ methanol.
abstract: Fixatives that contain methanol extract an unknown compound from several tissues including the retinas of squid (Loligo). We have determined that the compound probably contains (1) a myo-inositol ring that is phosphorylated in more than one position (including at the 5-hydroxyl), (2) a charged moiety that is not susceptible to alkaline phosphatase, and (3) a methyl group. We have found that the compound can be made by treating either phosphatidylinositol bisphosphate or human red cell ghosts with acidic methanol. We have confirmed the observation of Lips, Bross & Majerus [Proc. Natl. Acad. Sci. U.S.A. 85, 88-92] that the compound also can be made by methanolysis of inositol (cyclic 1:2,4,5)trisphosphate; however, we have not found inositol (cyclic 1:2,4,5)trisphosphate in either stimulated or unstimulated squid retinas. We tentatively identify the compound as (1-methylphosphoryl)inositol 4,5-bisphosphate formed by methanolysis of phosphatidylinositol 4,5-bisphosphate. By using this methanolysis to incorporate label from [14C]methanol, we have estimated the mass of inositol 1,4,5-trisphosphate in squid retinas to be approx. 30 mumol/l of retinal volume.
authors.affiliation: Department of Ophthalmology, Washington University School of Medicine, St. Louis, MO 63110.
authors.forename: J E
authors.initials: JE
authors.lastname: Brown
authors.forename: M
authors.initials: M
authors.lastname: Rudnick
authors.forename: A J
authors.initials: AJ
authors.lastname: Letcher
authors.forename: R F
authors.initials: RF
authors.lastname: Irvine
mesh_terms: D000469:Alkaline Phosphatase; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D049832:Decapodiformes; D004910:Erythrocyte Membrane / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D007295:Inositol Phosphates / Q000378:metabolism*; D007478:Iontophoresis; D000432:Methanol / Q000494:pharmacology*; D009609:Nitrous Oxide / Q000494:pharmacology; D010504:Periodic Acid / Q000494:pharmacology; D010744:Phosphoric Monoester Hydrolases / Q000378:metabolism; D012160:Retina / Q000187:drug effects / Q000378:metabolism; D013403:Sugar Phosphates / Q000378:metabolism*
chemical_list: D007295:Inositol Phosphates; D013403:Sugar Phosphates; D010504:Periodic Acid; C049924:inositol-1,2-cyclic-4,5-triphosphate; D000469:Alkaline Phosphatase; D010744:Phosphoric Monoester Hydrolases; D009609:Nitrous Oxide; D000432:Methanol