Synthesis and Evaluation of Nicotinic Acid Derived Tetrazines for Bioorthogonal Labeling
Synthesis and Evaluation of Nicotinic Acid Derived Tetrazines for Bioorthogonal Labeling
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DOI：
10.1055/s-0034-1380721
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发表时间：
2015-09-01
影响因子：
2.6
通讯作者：
Kele, Peter
中科院分区：
文献类型：
--
作者：
Cserep, Gergely B.;Demeter, Orsolya;Kele, Peter
合成了一组烟酸衍生的四嗪，并评价了其在与各种亲二烯体的逆电子需求Diels-Alder（IEDDA）反应中的活性。发现这些四嗪的性能受两个因素支配。理论和实验研究表明，空间效应可能会推翻积极预测的反应顺序。在反应性和稳定性之间做出折衷，将所选择的四嗪掺入脱氧核苷酸中以提供生物正交化的构建块，从而实现基于IEDDA的核酸标记方案。
A set of nicotinic acid derived tetrazines were synthesized and evaluated for activity in inverse-electron-demand Diels-Alder (IEDDA) reactions with various dienophiles. It was found that the performance of these tetrazines is governed by two factors. Theoretical and experimental investigations showed that steric effects may override the energetically predicted order of reactivity. Making a compromise between reactivity and stability, a selected tetrazine was incorporated into a deoxynucleotide to afford a bioorthogonalized building block enabling IEDDA-based tagging schemes of nucleic acids.