P-同手性寡聚（胸苷甲膦酸酯）的立体选择性合成。
Stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates).
作者信息
Lesnikowski Z J, Jaworska M, Stec W J
机构信息
Polish Academy of Sciences, Department of Bioorganic Chemistry, Lodz.
出版信息
Nucleic Acids Res. 1988 Dec 23;16(24):11675-89. doi: 10.1093/nar/16.24.11675.
Abstract
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.
摘要
描述了一种立体选择性合成磷同手性寡聚（胸苷甲膦酸酯）的方法。在具有活化5'-羟基功能的手性磷核苷酸组分5'-O-单甲氧基三苯甲基胸苷3'-O-[O-（4-硝基苯基）甲膦酸酯]（1）与3'-O-乙酰基胸苷（2）的立体特异性反应中制备了MMTrTPMeTAC（3）的完全保护的（Rp）-和（Sp）-非对映异构体。3中5'-OH基团的脱保护以及活化的5'-OH寡核苷酸组分与1的（Rp）-或（Sp）-异构体的后续逐步反应得到了三核苷酸MMTrTPMeTPMeTAC（4），随后得到了在其核苷酸间甲膦酸酯P原子处具有所有（Rp）-或所有（Sp）-构型的四核苷酸MMTrTPMeTPMeTPMeTAC（5）。
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