Abstract
New, spin-labeled nucleosides, and an efficient synthetic route for a modified uridine amidite, were developed. The spin-labeled part was the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) group, which was linked via an alkynyl chain at the 5 position of uridine. Three typical protecting groups, the t-butyldimethylsilyl (TBDMS) group at 2′, the dimethoxytrityl (DMTr) group at 5′, and the phosphoramidite group at 3′, were introduced to produce an automated nucleic acid synthesizer. The TEMPO group at the 5 position in the uridine structure affected introduction of bulky protecting groups, such as the DMTr group at the 5′ position and the TBDMS group at the 2′ position. The electron paramagnetic resonance (EPR) data revealed a nitroxyl radical in the structure of synthetic nucleoside compounds; however, RNA produced by automated synthesis using a TEMPO-linked uridine phosphoramidite building block was EPR silent.
| Original language | English |
|---|---|
| Journal | Synthetic Communications |
| DOIs | |
| Publication status | Accepted/In press - 2018 Jan 1 |
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Keywords
- 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)
- Electron paramagnetic resonance (EPR)
- RNA
- spin label
- unnatural nucleoside
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis of a protected ribonucleoside phosphoramidite-linked spin label via an alkynyl chain at the 5′ position of uridine. / Hatano, Akihiko; Terado, Nanae; Kanno, Yuichi; Nakamura, Toshikazu; Kawai, Gota.
In: Synthetic Communications, 01.01.2018.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of a protected ribonucleoside phosphoramidite-linked spin label via an alkynyl chain at the 5′ position of uridine
AU - Hatano, Akihiko
AU - Terado, Nanae
AU - Kanno, Yuichi
AU - Nakamura, Toshikazu
AU - Kawai, Gota
PY - 2018/1/1
Y1 - 2018/1/1
N2 - New, spin-labeled nucleosides, and an efficient synthetic route for a modified uridine amidite, were developed. The spin-labeled part was the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) group, which was linked via an alkynyl chain at the 5 position of uridine. Three typical protecting groups, the t-butyldimethylsilyl (TBDMS) group at 2′, the dimethoxytrityl (DMTr) group at 5′, and the phosphoramidite group at 3′, were introduced to produce an automated nucleic acid synthesizer. The TEMPO group at the 5 position in the uridine structure affected introduction of bulky protecting groups, such as the DMTr group at the 5′ position and the TBDMS group at the 2′ position. The electron paramagnetic resonance (EPR) data revealed a nitroxyl radical in the structure of synthetic nucleoside compounds; however, RNA produced by automated synthesis using a TEMPO-linked uridine phosphoramidite building block was EPR silent.
AB - New, spin-labeled nucleosides, and an efficient synthetic route for a modified uridine amidite, were developed. The spin-labeled part was the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) group, which was linked via an alkynyl chain at the 5 position of uridine. Three typical protecting groups, the t-butyldimethylsilyl (TBDMS) group at 2′, the dimethoxytrityl (DMTr) group at 5′, and the phosphoramidite group at 3′, were introduced to produce an automated nucleic acid synthesizer. The TEMPO group at the 5 position in the uridine structure affected introduction of bulky protecting groups, such as the DMTr group at the 5′ position and the TBDMS group at the 2′ position. The electron paramagnetic resonance (EPR) data revealed a nitroxyl radical in the structure of synthetic nucleoside compounds; however, RNA produced by automated synthesis using a TEMPO-linked uridine phosphoramidite building block was EPR silent.
KW - 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)
KW - Electron paramagnetic resonance (EPR)
KW - RNA
KW - spin label
KW - unnatural nucleoside
UR - http://www.scopus.com/inward/record.url?scp=85060129923&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85060129923&partnerID=8YFLogxK
U2 - 10.1080/00397911.2018.1545033
DO - 10.1080/00397911.2018.1545033
M3 - Article
AN - SCOPUS:85060129923
JO - Synthetic Communications
JF - Synthetic Communications
SN - 0039-7911
ER -