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1-(2′-Deoxy-β-D-xylofuranosyl)thymine Building Blocks for Solid-Phase Synthesis and Properties of Oligo(2′-Deoxyxylonucleotides)

✍ Scribed by Helmut Rosemeyer; Frank Seela

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
710 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

1-(2'-Deoxy-~-o-fhreo-pentofuranosyl)thymine ( = l-(2'-deoxy-~-~-xylofuranosyl)thymine; xT,; 2 ) was converted into its phosphonate 3b as well as its 2-cyanoethyl phosphoramidite 3c. Both compounds were used for solid-phase synthesis of d[(xT),,-TI (5), representing the first DNA fragment build up from 3'-5'-linked 2-deoxy-/l-D-xylonuckosides. Moreover, xT, was introduced into the innermost part of the self-complementary dodecamer d(G-T-A-G-A-A-xT-xT-C-T-A-C), (9). The CD spectrum of d[(xT)12-T] (5) exhibits reversed Cotton effects compared to d(T,,) (6; see Fig. I), implying a left-handed single strand. With d(AI2) (7) it could he hybridized to form a propably left-handed double strand d(AI2). d[(xT),,-T] ( 7 . 5 ) which was confirmed by melting experiments in combination with temperature-dependent CD spectroscopy. While 5 was hydrolyzed by snake-venom phosphodiesterase, it was resistant towards calf-spleen phosphodiesterase. The modified, self-complementary duplex 9 was hydrolyzed completely by snake-venom phosphodiesterase, at a twelvefold slower rate compared to unmodified 8; calf-spleen phosphodiesterase hydrolyzed 9 only partially.

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