[Study of asymmetrically substituted myo-inositols. XXXIX. The synthesis of conjugate of 2',3'-didehydro-3'-dehydroxythymidine with phosphatidylinositol: a new nucleoside phospholipid with potential anti-HIV activity].
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.
Shastina
N S
NS
Lomonosov State Academy of Fine Chemical Technology, pr. Vernadskogo 86, Moscow, 119571 Russia. biotechnology@mtu-net.ru
Tuchnaia
O A
OA
Eĭnisman
L I
LI
Kashiricheva
I I
II
Stepanov
A E
AE
Iurkevich
A M
AM
Shvets
V I
VI
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002625:Chemistry, Organic / Q000379:methods*; D007294:Inositol / Q000031:analogs & derivatives* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010716:Phosphatidylinositols / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D010743:Phospholipids / Q000737:chemistry; D010766:Phosphorylation; D019802:Succinic Acid / Q000737:chemistry; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
C478011:2',3'-didehydro-5'-(3-((1,2-dipalmitoylphosphatidylinositol-4-yl)carbonyl)propanoyl)thymidine; D019380:Anti-HIV Agents; D010716:Phosphatidylinositols; D010743:Phospholipids; D007294:Inositol; D019802:Succinic Acid; D013936:Thymidine