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Nucleic Acids Research, 1988, Vol. 16, No. 24 11675-11689
© 1988

CHEMISTRY

Stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates)

Zbigniew J. Lesnikowski, Maria Jaworska and Wojciech J. Stec

Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, Department of Bioorganic Chemistry Boczna 5, 90-362 Lodz, Poland

Received November 9, 1988. Accepted November 15, 1988.

An approach to the stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates) is described. Fully protected (Rp)- and (Sp)-diaste-reomers of MMTrTPMeTAC(3) were prepared in the stereospecific reaction of ira P-chiral nucleoide component 5' -O-monomethoxytrityithymidine 3' -O- [O- (4- nitrophenyl)methanephosphonate] (1) and 3'-O-acetylthymidine (2) bearing activated 5'-hydroxyl function. Deprotection of the 5'-OH group in 3 and subsequent stepwise reactions of activated 5'-OH oligonucleo tide components with (Rp)- or (Sp)- isomers of 1 gave the trinucleotide MMTrTPMeTAc (4) and, subsequently, the tetranucleotide MMTrTPMeTPMeTAc (5) possessing all (Rp) - or all (Sp) - configurations at their internucleotide methanephosphonate P-atome.


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