Nucleobase-caged peptide nucleic acids: PNA/PNA duplex destabilization and light-triggered PNA/PNA recognition
Nucleobase-caged peptide nucleic acids: PNA/PNA duplex destabilization and light-triggered PNA/PNA recognition
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DOI：
10.1002/psc.2514
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发表时间：
2013-07-01
影响因子：
2.1
通讯作者：
Diederichsen, Ulf
中科院分区：
文献类型：
--
作者：
Guha, Samit;Graf, Julia;Diederichsen, Ulf
N-（2-氨基乙基）甘氨酸肽核酸（aeg-PNA）中的2-（o-硝基苯基）-丙基（NPP）基团作为笼化基团来屏蔽腺嘌呤和胞嘧啶。利用NPP核碱基保护基团对Fmoc裂解、偶联、旋盖和树脂裂解条件的高稳定性，通过Fmoc固相合成法合成了腺嘌呤基和胞嘧啶基核氨基酸构建基Fmoc- anpp - aegoh和Fmoc- cnpp - aegoh，并将其整合到PNA序列中。在365nm紫外- led照射下去除核碱基笼化基团。核碱基笼化基团提供了影响沃森-克里克碱基配对的空间拥挤，从而影响了PNA双链的稳定性。双链形成可以完全抑制互补PNA在两条链中含有笼化基团。PNA/PNA识别可以通过紫外光触发释放光致保护基团来完全恢复。版权所有(c) 2013欧洲多肽协会和约翰威利父子有限公司
The 2-(o-nitrophenyl)-propyl (NPP) group is used as caging group to mask the nucleobases adenine and cytosine in N-(2-aminoethyl)glycine peptide nucleic acids (aeg-PNA). The adeninyl and cytosinyl nucleo amino acid building blocks Fmoc-aNPP-aeg-OH and Fmoc-cNPP-aeg-OH were synthesized and incorporated into PNA sequences by Fmoc solid phase synthesis relying on high stability of the NPP nucleobase protecting group toward Fmoc-cleavage, coupling, capping, and resin cleavage conditions. Removal of the nucleobase caging group was achieved by UV-LED irradiation at 365nm. The nucleobase caging groups provided sterical crowding effecting the Watson-Crick base pairing, and thereby, the PNA double strand stabilities. Duplex formation can completely be suppressed for complementary PNA containing caging groups in both strands. PNA/PNA recognition can be completely restored by UV light-triggered release of the photolabile protecting group. Copyright (c) 2013 European Peptide Society and John Wiley & Sons, Ltd.