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Nucleic Acids Research, 1994, Vol. 22, No. 11 2022-2027
© 1994

CHEMISTRY

Sterical recognition by T4 polynucleotide kinase of non-nucleosidic moieties 5'-attached to oligonucleotides

Marie-Laurence Fontanel, Hervé Bazin1,* and Robert Téoule

CEA/Département de Recherche Fondamentale sur la matière condensée/SESAM 38054 Grenoble Cedex 9 1Laboratoire des Sondes Moléculaires CIS Bio international, BP32-91192 Gif-sur-Yvette, Cedex, France

*To whom correspondence should be addressed

Received March 15, 1994. Accepted April 25, 1994.

The ability of T4 polynucleotide kinase (PNK) to phosphorylate non-nucleosidic moieties 5'-attached to oligodeoxynucleotides (ODNs) has been investigated. Non-nucleosidic phosphoramidite units were prepared from ethane-1,2-diol and propane-1,3-diol backbones. Some of them corresponded to pure enantiomers. They were used to obtain the corresponding 5'-end modified oligothymidylates X(pdT)10. The free primary hydroxyl of the non-nucleosidic moieties (X) of these oligomers was phosphorylated by PNK. We report the stereo-selective phosphorylation of the L form of the 5'-end attached non-nucleosidic chiral fragments; the non-chiral moieties were completely phosphorylated. Dimers of glycerol analogue and thymidine 3'-phosphate were not recognized by PNK and the shortest modified ODN able to be phosphorylated was a trinucleotide X(pdT)3. A modified X(pdT)10, bearing a cyclic abasic site (X) at its 5'-end, was prepared by chemical synthesis from 1,2-dideoxyribose phosphoramidite and was phosphorylated with a 90% yield.


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