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Diastereomers of thymidine 3'-O-(methanephosphonothioate): synthesis, absolute configuration and reaction with 3'-methoxyacetylthymidine under conditions of triester approach to oligonucleotide synthesis.

作者信息

Niewiarowski W, Leśnikowski Z J, Wilk A, Guga P, Okruszek A, Uznański B, Stec W

机构信息

Department of Bioorganic Chemistry, Polish Academy of Sciences, Lódź.

出版信息

Acta Biochim Pol. 1987;34(2):217-31.

PMID:3673443
Abstract

Diastereomers of the title compound were obtained and absolute configuration was assigned by means of stereochemical correlation. Their reaction with 3'-O-methoxyacetylthymidine in the presence of triisopropylbenzenesulphonyl (4-nitro) triazole is neither chemo- nor stereo-selective and leads to diastereomeric pairs of dithymidyl (3',5')methanephosphonate and -methanephosphonothioate. Obtained results are discussed in terms of mechanism of activation of phosphodiesters under conditions known as "phosphotriester approach to oligonucleotide synthesis".

摘要

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引用本文的文献

1
Synthesis and thermodynamics of oligonucleotides containing chirally pure R(P) methylphosphonate linkages.含手性纯R(P)甲基膦酸酯键的寡核苷酸的合成与热力学
Nucleic Acids Res. 1996 Nov 15;24(22):4584-91. doi: 10.1093/nar/24.22.4584.
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
Nucleic Acids Res. 1990 Apr 25;18(8):2109-15. doi: 10.1093/nar/18.8.2109.