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Nucleotides. Part LVI. Synthesis and biological activity of modified (2′–5′)triadenylates containing 2′-terminal 2′,3′-dideoxy-3′-fluoroadenosine derivatives

✍ Scribed by Evgeny I. Kvasyuk; Tamara I. Kulak; Olga V. Tkachenko; Svetlana L. Sentyureva; Igor A. Mikhailopulo; Robert J. Suhadolnik; Earl E. Henderson; Susan E. Horvath; Ming-Xu Guan; Wolfgang Pfleiderer

Publisher
John Wiley and Sons
Year
1998
Tongue
German
Weight
446 KB
Volume
81
Category
Article
ISSN
0018-019X

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✦ Synopsis

Fakultit fur Chemie, Universitat Konstanz, Postfach 5560, D-78434 Konstanz Some new (2'-5')triadenylates 13-16, containing at the 2'-terminal end 3'-fluoro-2,3'-dideoxyadenosine derivatives, have been synthesized by the phosphotriester method. The selectively blocked nucleosides 2,4,5, and 7 were synthesized from the corresponding unprotected nucleosides 1, 3, and 6 . The synthesized trimers 13 and 14 were 4-and &fold, respectively, more stable towards phosphodiesterase from Crorulus durissus than the natural trimer 17. In comparison to trimer 17 the new compounds 13-15 inhibit HIV-I reverse transcriptase (RT) activity, and 15and 16 the HIV-I induced syncytia formation 2-3 fold whereas none of 13-16can improve RNase L activity.

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