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Synthesis of a phosphoramidite of 2′-deoxy-5,6-dihydro-5-azacytidine. Its potential application in the synthesis of DNA containing dihydro-5-aza-and 5-azacytosine bases.

✍ Scribed by Amanda J. Goddard; Victor E. Marquez

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
260 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel phosphoramidite (9) has been synthesized and shown to be an efficient coupling reagent for the synthesis ofoligonucleotide fragments containing the modified base 5,6-dihydro-5-azacytosine. With a model dihydro-5_azacytosine/thymine dimer (z), oxidation of the dihydrotriazine ring to the aromatic base was partially successful. In view of the well established relationship that exists between the DNA incorporation of 5-azacytosine residues and gene activation,l we became interested in developing a suitable methodology for the synthesis of oligonucleotide fragments containing this unnatural base. These modified oligonucleotides, which would contain 5-azacytosine residues at specific sites, could serve as tools for elucidating the mechanism of selective gene activation and the relationship that exists between the presence of the triazine base and inhibition of DNA methy1ation.l

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