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Synthesis of 1,1,2-trisubstituted cyclopropane nucleosides in enantiomerically pure forms
Nucleosides, Nucleotides & Nucleic Acids ( IF 1.3 ) Pub Date : 2019-06-12 , DOI: 10.1080/15257770.2019.1625380
Daichi Fushihara 1, 2 , Hayato Fukuda 1 , Hiroshi Abe 2 , Satoshi Shuto 1, 3
Affiliation  

Abstract Due to the unique rigid and small steric feature of cyclopropane, cyclopropane nucleosides (CPNs) in which the ribose (deoxyribose) of nucleosides are replaced by a hydroxy-substituted cyclopropane, are of great biological interest. Novel 1,1,2-trisubstituted cyclopropane nucleosides were synthesized in enantiomerically pure forms as potential antiviral agents. In the synthesis, two cyclopropane tosylates, which were prepared from chiral cyclopropane lactones previously reported by us, were used effectively as common intermediates for the CPNs. These CPNs are also potentially useful as nucleoside units to incorporate into oligonucleotides in nucleic acids chemotherapy studies.

中文翻译:

对映异构纯形式的 1,1,2-三取代环丙烷核苷的合成

摘要 由于环丙烷独特的刚性和小空间特征,其中核苷的核糖(脱氧核糖)被羟基取代的环丙烷取代的环丙烷核苷(CPNs)具有重要的生物学意义。新型 1,1,2-三取代的环丙烷核苷以对映体纯形式合成,作为潜在的抗病毒剂。在合成中,由我们先前报道的手性环丙烷内酯制备的两种环丙烷甲苯磺酸盐被有效地用作 CPN 的常用中间体。在核酸化学疗法研究中,这些 CPNs 还可能用作核苷单位以整合到寡核苷酸中。
更新日期:2019-06-12
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