Stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates).
An approach to the stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates) is described. Fully protected (Rp)- and (Sp)-diastereomers of MMTrTPMeTAC (3) were prepared in the stereospecific reaction of P-chiral nucleotide component 5'-O-monomethoxytritylthymidine 3'-O-[O-(4-nitrophenyl)methanephosphonate] (1) and 3'-O-acetylthmydine (2) bearing activated 5'-hydroxyl function. Deprotection of the 5'-OH group in 3 and subsequent stepwise reactions of activated 5'-OH oligonucleotide components with (Rp)- or (Sp)- isomers of 1 gave the trinucleotide MMTrTPMeTPMeTAC (4) and, subsequently, the tetranucleotide MMTrTPMeTPMeTPMeTAC (5) possessing all (Rp)- or all (Sp)- configurations at their internucleotide methanephosphonate P-atoms.
Lesnikowski
Z J
ZJ
Polish Academy of Sciences, Department of Bioorganic Chemistry, Lodz.
Jaworska
M
M
Stec
W J
WJ
D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D009841:Oligonucleotides; D009946:Organothiophosphorus Compounds; D013936:Thymidine