脱氧核糖核苷硫代磷酸酯的重新研究：脱氧核糖核苷-3′-亚磷酸二甲酯的合成与性质

Reinvestigation of deoxyribonucleoside phosphorothioites: synthesis and properties of deoxyribonucleoside-3' dimethyl phosphites.

作者信息

Nagai H, Fujiwara T, Fujii M, Sekine M, Hata T

机构信息

Department of Life Chemistry, Tokyo Institute of Technology, Yokohama, Japan.

出版信息

Nucleic Acids Res. 1989 Nov 11;17(21):8581-93. doi: 10.1093/nar/17.21.8581.

DOI:10.1093/nar/17.21.8581

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC335029/

Abstract

Further investigation of the synthesis of deoxyribonucleoside-3' (t-butyl) O-(2-cyanoethyl) phosphorothioites as monomer building units for the phosphorothioite approach has led us to conclude that internucleotidic bond formation proceeded via bis(deoxyribonucleoside-3') (2-cyanoethyl) phosphite intermediates, which proved to be activated by iodine, rather than the mechanism previously reported. In connection with this study, deoxyribonucleoside-3' dimethyl phosphites were synthesized and detailed properties of them are also described.

摘要

对作为亚磷硫酯法单体构建单元的脱氧核糖核苷-3'（叔丁基）O-（2-氰基乙基）亚磷硫酯合成的进一步研究使我们得出结论，核苷酸间键的形成是通过双（脱氧核糖核苷-3'）（2-氰基乙基）亚磷酸酯中间体进行的，事实证明该中间体可被碘激活，而非先前报道的机制。与此研究相关，合成了脱氧核糖核苷-3' 亚磷酸二甲酯，并对其详细性质进行了描述。

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Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product.聚合物载体寡核苷酸合成 XVIII：脱氧核苷的β-氰基乙基-N，N-二烷基氨基-/N-吗啉代亚磷酰胺用于 DNA 片段合成，简化最终产物的脱保护和分离

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Synthesis of oligoribonucleotides based on the facile cleavage of methyl phosphotriester intermediates.基于甲基磷酸三酯中间体的简便裂解合成寡核糖核苷酸。

J Am Chem Soc. 1977 May 11;99(10):3526-8. doi: 10.1021/ja00452a069.

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