- Synthesis of formacetal-linked dinucleotides to facilitate dsDNA bending and binding to the homeodomain of Pax6
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Two formacetal-linked dinucleotides T∧T and T∧A were synthesized as phosphoramidite building blocks for solid-phase synthesis. Incorporated in a 29-mer DNA, the oligomers P3T∧T and P3T∧A were studied with respect to the binding activ
- Pitulescu, Marian,Grapp, Marcel,Kraetzner, Ralph,Knepel, Willhart,Diederichsen, Ulf
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experimental part
p. 2100 - 2106
(2009/04/05)
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- An alternative route to the preparation of (3' → 5') methylene acetal linked di- and trinucleosides
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Reaction of deoxynucleoside 3'-O-(methylthiomethyl) acetals 1 with N-iodosuccinimide (NlS) and dibutyl phosphate furnished the corresponding 3'-O-(dibutoxyphosphoryloxy)methyl acetals 6. Condensation of the latter with appropriately protected deoxynucleoside acceptors 3, in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), afforded in most cases the (3' → 5') methylene acetal linked d(B(1Λ) B2) dimers 4. In addition, TMSOTf-promoted coupling of donor 6 (B1 = C(Bz)) with 3'-O-(methylthiomethyl)thymidine (8) yielded dimer 9. Reaction of 9 with NIS and dibutyl phosphate gave dimer 10, which was applied successfully in the TMSOTf-assisted fusion with acceptors 3 (B2 = C(Bz) and A(Bz)), to afford the corresponding trimers d(C(Λ)T(Λ)C) 11 and d(C(Λ)T(Λ)A) 12.
- Quaedflieg,Timmers,Van Der Marel,Kuyl-Yeheskiely,Van Boom
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p. 627 - 633
(2007/10/02)
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