Cysteine based PNA (CPNA): design and synthesis of novel CPNA monomers.
Cysteine based PNA (CPNA): design and synthesis of novel CPNA monomers.
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基于半胱氨酸的 PNA (CPNA)：新型 CPNA 单体的设计和合成。
DOI：
10.1007/978-0-387-73657-0_243
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发表时间：
2009
影响因子：
--
通讯作者：
McLaughlin,MarkL
中科院分区：
文献类型：
--
作者：
Yi,SungWook;Jain,Priyesh;Ajmera,Mehul;Kaulagari,SridharReddi;Topper,Melissa;Anderson,Laura;McLaughlin,MarkL
肽核酸（PNAs）是一类伪肽DNA模拟物，由Nielsen及其同事于1991年首次引入[1]。PNA寡聚体通过Watson-Crick碱基配对与互补DNA和RNA链形成非常稳定的序列特异性双链体，并可通过螺旋侵入与双链体DNA结合[2]。PNA的这些有趣的性质暗示了其在医学和生物技术应用上的巨大潜力。毫不奇怪，自从发现以来，各种科学团体都报道了关于PNA合成及其应用的巨大努力。然而，可能由于简单中性主链的性质，大多数PNA寡聚物显示出差的水溶性和细胞渗透性，这些问题已经成为PNA在生物医学领域应用的主要障碍[3]。为了改善这些特性，科学家们一直在连接细胞膜透化肽序列，并试图修饰PNA的骨架，迄今为止只有少数例子显示出一些积极的改善[4]。在这份报告中，我们介绍了我们的合成新的半胱氨酸为基础的PNA单体与各种烷基链连接，如图1所示。与其他氨基酸不同，半胱氨酸具有使PNA合成复杂化的硫醇基团，这大概是从未报道过基于半胱氨酸的PNA的原因。我们已经设想，半胱氨酸的巯基可以作为设计用于改善PNA寡聚物的物理性质的基团的附着位点。
Peptide nucleic acids (PNAs), a class of pseudo-peptide DNA mimics, were first introduced by Nielsen and his coworkers in 1991 [1]. PNA oligomers form very stable sequence-specific duplexes with complementary DNA and RNA strands through Watson-Crick base paring, and can bind to duplex DNA by helix invasion [2]. These intriguing properties of PNA implicated great potential for medical and biotechnical applications. Not surprisingly, tremendous efforts on the synthesis of PNAs and their applications have been reported from various scientific groups since their discovery. However, owing presumably to the nature of the simple neutral backbones, most of PNA oligomers have shown poor water-solubility and cell permeability, and these problems have been the main stumbling blocks for PNA application in biomedical fields [3]. To improve these properties, scientists have been attaching cell-membrane-permeabilizing peptide sequences and trying to modify the backbone of PNA, and only a few examples have shown some positive improvement to date [4]. In this report, we introduce our synthesis of novel cysteine based PNA monomers with various alkyl chains attached as shown in Figure 1. Unlike other amino acids, the cysteine possesses the thiol group which complicates the PNA synthesis and that is presumably why cysteine based PNAs have never been reported. We have envisioned that the thiol group of cysteine could take the role as an attachment site for groups designed to improve the physical properties of the PNA oligomers.
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DOI：
10.1042/bj2470141
发表时间：
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期刊：
The Biochemical journal
影响因子：
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