Synthesis and Properties of 2′-Deoxyadenosine Mimics Bearing a Thieno[3,2-d]pyrimidine Ring

被引：0
作者：
Fuchi, Yasufumi [1 ]
Kawaguchi, Miho [1 ]
Ito, Yuta [1 ]
Hari, Yoshiyuki [1 ]
机构：
[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro Cho, Nishihama, Tokushima 7708514, Japan
来源：
SYNLETT | 2024年 / 35卷 / 06期
关键词：
C-nucleoside; adenosine mimic; thienopyrimidine; oligonucleotide; fluorescence; ADENOSINE-DEAMINASE; C-NUCLEOSIDES; FORMYCIN-B; ANALOG; PSEUDOURIDINE; INHIBITORS; RESIDUES;
D O I：
10.1055/s-0042-1751508
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A C-nucleoside with a stable C-C glycosidic bond can be used as a building block for chemically modified oligonucleotides (ONs).In this study, two adenosine-like C-nucleosides (d(S)A and d(SO2)A) bearing thieno[3,2-d]pyrimidine rings were designed and synthesized. These analogues were synthesized via the Heck reaction, and their properties as monomer nucleosides were investigated. Both the d(S)A and d(SO2)Amonomers were not recognized by adenosine deaminase (ADA). In addition, they exhibited fluorescence emissions in the UV and visible regions of d(S)A and d(SO2)A, respectively. Subsequently, d(S)A was converted into a phosphoramidite compound and incorporated into the ONs. The synthesized d(S)A-modified ONs formed a stable duplex with DNA and RNA complements comparable to natural adenosine. Furthermore, the modified ONs exhibited fluorescence emission derived from d(S)A
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页码：716 / 720
页数：5
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