Synthesis and incorporation into a-DNA of a novel conformationally constrained alpha-nucleoside analogue

Keller, B. M.; Leumann, Christian (2002). Synthesis and incorporation into a-DNA of a novel conformationally constrained alpha-nucleoside analogue. Synthesis - journal of synthetic organic chemistry, 2002(06), pp. 789-796. Thieme 10.1055/s-2002-25755

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We describe the synthesis and incorporation into alpha-DNA of a novel conformationally constrained alpha-nucleoside analogue. The carbohydrate part of this analogue was prepared in 4 steps from the known bicyclic precursor 1 via a stereospecific, intramolecular, Et 3B mediated radical addition to a keto-function as the key step. The thus obtained intermediate 4 was transformed stereoselectively into the corresponding alpha-nucleoside analogues 7 and 8 containing the bases adenine and thymine, and were further elaborated into the phosphoramidite building blocks 11 and 12 . Both building blocks were incorporated into alpha-oligodeoxynucleotides and their pairing behavior to parallel complementary DNA studied by UV-melting experiments. Single substitutions of alpha-deoxyribnucleoside units by the new analogues in the center of duplexes were found to be thermally destabilizing by only -0.8 to -3.1›C.

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