title: Synthesis of optically-active hexadecyl thiophosphoryl-1-D-myo-inositol: a thiophosphate analog of phosphatidylinositol.
abstract: The synthesis of optically-active hexadecyl thiophosphoryl-1-D-myo-inositol 11 was accomplished from 2,3-O-(D-1',7',7'-trimethyl[2.2.1]bicyclohept-2'-ylidene)-4,5,6-O- tris(methoxymethyl)-D-myo-inositol 6 or 2,3,4,5,6-O-pentakis(methoxymethyl)-D-myo-inositol 14, using the Arbusov reaction of their dimethyl phosphite derivatives 7 and 15 with N-hexadecyl thiophthalimide 8. This product was a substrate for phosphatidylinositol-specific phospholipase C from Bacillus cereus.
authors.affiliation: Department of Chemistry, St Olaf College, Northfield, MN.
authors.forename: A S
authors.initials: AS
authors.lastname: Bushnev
authors.forename: E K
authors.initials: EK
authors.lastname: Hendrickson
authors.forename: V I
authors.initials: VI
authors.lastname: Shvets
authors.forename: H S
authors.initials: HS
authors.lastname: Hendrickson
mesh_terms: D001409:Bacillus cereus / Q000378:metabolism; D066298:In Vitro Techniques; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D043265:Phosphatidylinositol Diacylglycerol-Lyase; D010716:Phosphatidylinositols / Q000138:chemical synthesis* / Q000737:chemistry; D054801:Phosphoinositide Phospholipase C; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D010716:Phosphatidylinositols; C089676:hexadecyl thiophosphoryl-1-myo-inositol; D010727:Phosphoric Diester Hydrolases; D054801:Phosphoinositide Phospholipase C; D043265:Phosphatidylinositol Diacylglycerol-Lyase