Abstract
A partially protected phosphatidylinositol with a free hydroxyl group in the cyclitol moiety was synthesized by phosphorylation of a tetrasubstituted myo-inositol using the H-phosphonate and phosphoamidite methods. The H-phosphonate method was advantageous for the synthesis of selectively protected monophosphoinositide due to a lesser number of stages. Two schemes for the conjugation of 2',3'-didehydro-3'-dehydroxythymidine with phosphatidylinositol using succinic acid as a linker were tested in the synthesis of the target nucleoside phospholipid.
MeSH terms
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Anti-HIV Agents / chemical synthesis*
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Anti-HIV Agents / pharmacology
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Chemistry, Organic / methods*
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Inositol / analogs & derivatives*
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Inositol / chemistry*
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Phosphatidylinositols / chemical synthesis*
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Phosphatidylinositols / chemistry*
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Phosphatidylinositols / pharmacology
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Phospholipids / chemistry
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Phosphorylation
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Succinic Acid / chemistry
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Thymidine / analogs & derivatives
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Thymidine / chemical synthesis*
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Thymidine / chemistry*
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Thymidine / pharmacology
Substances
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2',3'-didehydro-5'-(3-((1,2-dipalmitoylphosphatidylinositol-4-yl)carbonyl)propanoyl)thymidine
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Anti-HIV Agents
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Phosphatidylinositols
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Phospholipids
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Inositol
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Succinic Acid
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Thymidine