Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation
Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation
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DOI：
10.1186/1860-5397-2-23
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发表时间：
2006-11-30
影响因子：
2.7
通讯作者：
Kois, Pavol
中科院分区：
文献类型：
--
作者：
Kosiova, Ivana;Janicova, Andrea;Kois, Pavol
背景：叠氮化物与三芳基膦在温和条件下反应生成亚胺磷烷，亚胺磷烷可以与几乎任何一种亲电试剂反应，如醛/酮生成亚胺或酯生成酰胺。这种所谓的Staudinger连接已被广泛应用于生物偶联的一般工具，包括核酸的特异性标记。结果：描述了一种通过分子间Staudinger连接制备标记核苷的新方法。叠氮核苷与三苯基膦反应生成亚磷烷中间体，随后与香豆素或二茂铁衍生物反应生成香豆素或二茂铁标记核苷。香豆素标记核苷的荧光特性被确定。结论：通过分子间Staudinger连接制备了新的香豆素和二茂铁标记核苷。该反应将荧光香豆素和生物特异性核苷结合到具有良好荧光和电化学性能的新分子中。分离产物的产率取决于叠氮核苷和羧酸的结构。对核苷底物的Staudinger连接动力学的详细研究正在进行中。
Background: Reaction of azides with triaryl phosphines under mild conditions gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e. g. aldehydes/ ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of nucleic acids.Results: A new approach for the preparation of labeled nucleosides via intermolecular Staudinger ligation is described. Reaction of azidonucleosides with triphenylphosphine lead to iminophosphorane intermediates, which react subsequently with derivatives of coumarin or ferrocene to form coumarin or ferrocene labeled nucleosides. Fluorescent properties of coumarin labeled nucleosides are determined.Conclusion: New coumarin and ferrocene labeled nucleosides were prepared via intermolecular Staudinger ligation. This reaction joins the fluorescent coumarin and biospecific nucleoside to the new molecule with promising fluorescent and electrochemical properties. The isolated yields of products depend on the structure of azidonucleoside and carboxylic acids. A detailed study of the kinetics of the Staudinger ligation with nucleoside substrates is in progress.