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1
Stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates).P-同手性寡聚（胸苷甲膦酸酯）的立体选择性合成。
Nucleic Acids Res. 1988 Dec 23;16(24):11675-89. doi: 10.1093/nar/16.24.11675.
2
Octa(thymidine methanephosphonates) of partially defined stereochemistry: synthesis and effect of chirality at phosphorus on binding to pentadecadeoxyriboadenylic acid.部分确定立体化学结构的八（胸苷甲膦酸酯）：磷原子手性对与十五聚脱氧核糖腺苷酸结合的合成及影响
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4
Studies on stereospecific formation of P-chiral internucleotide linkage: synthesis of all-Rp and all-Sp methylphosphonate pentanucleotide d(MMTrAPMeTPMeTPMeCPMeTAc) via Grignard activated coupling.P-手性核苷酸间键的立体特异性形成研究：通过格氏试剂活化偶联合成全-Rp和全-Sp甲基膦酸酯五核苷酸d(MMTrAPMeTPMeTPMeCPMeTAc)
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6
Diastereomeric dinucleoside-methylphosphonates: determination of configuration with the 2-D NMR ROESY technique.非对映异构二核苷甲基膦酸酯：用二维核磁共振ROESY技术确定构型
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7
Octa(thymidine methanephosphonates) of partially defined stereochemistry: synthesis and effect of chirality at phosphorus on binding to pentadecadeoxyriboadenylic acid.部分确定立体化学结构的八（胸苷甲膦酸酯）：磷原子手性对与十五聚脱氧核糖腺苷酸结合的合成及影响
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Proton nuclear magnetic resonance studies on dideoxyribonucleoside methylphosphonates.
Biochemistry. 1980 May 13;19(10):2122-32. doi: 10.1021/bi00551a020.
2
Molecular structure of deoxyadenylyl-3'-methylphosphonate-5'-thymidine dihydrate, (d-ApT x 2H2O), a dinucleoside monophosphate with neutral phosphodiester backbone. An X-ray crystal study.二水合脱氧腺苷-3'-甲基膦酸酯-5'-胸苷（d-ApT·2H₂O）的分子结构，一种具有中性磷酸二酯主链的二核苷单磷酸。X射线晶体学研究。
Nucleic Acids Res. 1983 May 11;11(9):2801-14. doi: 10.1093/nar/11.9.2801.
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Inducible repair of phosphotriesters in Escherichia coli.大肠杆菌中磷酸三酯的可诱导修复
Proc Natl Acad Sci U S A. 1983 Dec;80(24):7380-4. doi: 10.1073/pnas.80.24.7380.
4
Oligothymidylate analogues having stereoregular, alternating methylphosphonate/phosphodiester backbones. Synthesis and physical studies.具有立体规则交替甲基膦酸酯/磷酸二酯主链的寡聚胸苷酸类似物。合成与物理研究。
J Biol Chem. 1980 Oct 25;255(20):9659-65.
5
Syntheses and properties of adenine and thymine nucleoside alkyl phosphotriesters, the neutral analogs of dinucleoside monophosphates.腺嘌呤和胸腺嘧啶核苷烷基磷酸三酯（二核苷单磷酸的中性类似物）的合成与性质
J Am Chem Soc. 1971 Dec;93(24):6657-65. doi: 10.1021/ja00753a054.
6
Hybridization arrest of globin synthesis in rabbit reticulocyte lysates and cells by oligodeoxyribonucleoside methylphosphonates.寡脱氧核糖核苷甲基膦酸酯对兔网织红细胞裂解物和细胞中珠蛋白合成的杂交抑制作用。
Biochemistry. 1985 Oct 22;24(22):6139-45. doi: 10.1021/bi00343a016.
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Effects of pendant groups at phosphorus on binding properties of d-ApA analogues.磷原子上侧基对d-ApA类似物结合特性的影响。
Nucleic Acids Res. 1986 Apr 25;14(8):3487-99. doi: 10.1093/nar/14.8.3487.
8
B- to Z-DNA transition probed by oligonucleotides containing methylphosphonates.含甲基膦酸酯的寡核苷酸对B型到Z型DNA转变的探测
Proc Natl Acad Sci U S A. 1986 Mar;83(6):1617-21. doi: 10.1073/pnas.83.6.1617.
9
Molecular structure of a deoxyribose-dinucleotide, sodium thymidylyl-(5' yields to 3')-thymidylate-(5') hydrate (pTpT), and a possible structural model for polythymidylate.脱氧核糖二核苷酸——胸苷酰基 -（5' 至 3'）-胸苷酸酯 -（5'）水合物（pTpT）的分子结构以及聚胸苷酸的一种可能结构模型。
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10
Intimate details of the conformational characteristics of deoxyribodinucleoside monophosphates in aqueous solution.脱氧核糖核苷单磷酸在水溶液中的构象特征的详细信息。
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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.

DOI:10.1093/nar/16.24.11675
PMID:3211747
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC339103/
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）。