6-Phenylpyrrolocytidine: An Intrinsically Fluorescent, Environmentally Responsive Nucleoside Analogue.
6-Phenylpyrrolocytidine: An Intrinsically Fluorescent, Environmentally Responsive Nucleoside Analogue.
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DOI：
10.1002/cpnc.75
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发表时间：
2019-03-01
影响因子：
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通讯作者：
Hudson, Robert H E
中科院分区：
文献类型：
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作者：
Cho, Sung Ju;Ghorbani-Choghamarani, Arash;Hudson, Robert H E
报道了与2‘-脱氧和核糖核酸基-6-苯基吡咯胞苷的标准、自动化寡核苷酸合成相容的亚胺试剂的详细合成方案。每个方案从母体核苷开始，并制备5‘-O-二甲氧基三苯基-N4-苯甲酰基-5-碘胞嘧啶衍生物，用于碱基修饰化学。关键步骤是通过一锅Pd催化的Sonogashira交叉偶联反应和5-内切环合反应直接合成6-苯基吡咯胞嘧啶苷元。随后的标准转化提供了脱氧和2‘-O-叔丁基二甲基硅基保护的核糖核苷亚磷酰胺试剂。©2019 John Wiley&Sons，Inc.
The detailed synthetic protocols for the preparation of phosphoramidite reagents compatible with standard, automated oligonucleotide synthesis for the 2'-deoxy- and ribo-6-phenylpyrrolocyitidine are reported. Each protocol starts with the parent nucleoside and prepares the 5'-O-dimethoxytrityl-N4 -benzoyl-5-iodocytosine derivative for the nucleobase modification chemistry. The key step is the direct formation of 6-phenylpyrrolocytosine aglycon via a sequential, one-pot Pd-catalyzed Sonogashira-type cross- coupling followed by a 5-endo-dig cyclization. Subsequent standard transformations provide the deoxy- and 2'-O-tert-butyldimethysilyl protected ribo- nucleoside phosphoramidite reagents. © 2019 by John Wiley & Sons, Inc.