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核苷氢硼膦酸酯的化学合成及其作为磷修饰核苷酸类似物前体的应用。

Chemical synthesis of nucleoside H-boranophosphonates and their application as precursors of P-modified nucleotide analogues.

作者信息

Oka Natsuhisa, Higashida Renpei, Takayama Yuji, Ando Kaori, Wada Takeshi

机构信息

Department of Chemistry, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan.

出版信息

Nucleic Acids Symp Ser (Oxf). 2009(53):111-2. doi: 10.1093/nass/nrp056.

DOI:10.1093/nass/nrp056
PMID:19749285
Abstract

Nucleoside H-boranophosphonates were synthesized via the condensation reactions of appropriately protected nucleosides with monopyridinium H-boranophosphonate and subsequent deprotection under basic conditions. 3',5'-O-Protected dinucleoside H-boranophosphonates were also synthesized via the condensation of the corresponding 5'-O-protected nucleoside 3'-H-boranophosphonates with 3'-O-protected nucleosides. A study on the chemical properties of the resultant dinucleoside phosphate analogues revealed that the P-H group could be further modified under anhydrous basic conditions.

摘要

通过适当保护的核苷与单吡啶鎓氢硼烷膦酸酯的缩合反应,随后在碱性条件下脱保护,合成了核苷氢硼烷膦酸酯。还通过相应的5'-O-保护的核苷3'-氢硼烷膦酸酯与3'-O-保护的核苷的缩合反应,合成了3',5'-O-保护的二核苷氢硼烷膦酸酯。对所得二核苷磷酸类似物的化学性质的研究表明,P-H基团在无水碱性条件下可以进一步修饰。

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