Synthesis of optically-active hexadecyl thiophosphoryl-1-D-myo-inositol: a thiophosphate analog of phosphatidylinositol.
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.
Bushnev
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AS
Department of Chemistry, St Olaf College, Northfield, MN.
Hendrickson
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EK
Shvets
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Hendrickson
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HS
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
D010716:Phosphatidylinositols; C089676:hexadecyl thiophosphoryl-1-myo-inositol; D010727:Phosphoric Diester Hydrolases; D054801:Phosphoinositide Phospholipase C; D043265:Phosphatidylinositol Diacylglycerol-Lyase